Substituted 3-phenylpyrazoles

ABSTRACT

Substituted 3-phenylpyrazoles I ##STR1## are used as herbicides.

This application is a 371 of PCT/EP95/02062 filed May 31, 1995.

The present invention relates to novel substituted 3-phenylpyrazoles of the formula I ##STR2## where R¹ is --C(R⁸)═C(R⁷,R¹²), ##STR3## --C(R⁹, R¹⁰)--C(R⁸,R¹¹,R¹²), ##STR4## --C(R⁹)═C(R⁸)-phenyl or --C(R⁹,R¹⁰)--C(R⁸,R¹³)-phenyl, in which each phenyl ring may if desired carry from one to three substituents selected form the group consisting of nitro, cyano, fluorine, chlorine, bromine, trifluoromethyl, hydroxyl, hydroxycarbonyl, C₁ -C₄ -alkoxy and (C₁ -C₄ -alkoxy ) carbonyl;

R² is cyano, trifluoromethyl or halogen;

R³ is hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl or C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl;

R⁴ is C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄ -alkylsulfinyl, C₁ -C₄ -halo-alkylsulfinyl, C₁ -C₄ -alkylsulfonyl or C₁ -C₄ -haloalkylsulfonyl;

R⁵ is hydrogen, nitro, halogen, --COOR¹⁵ or --CO--N(R¹⁶,R¹⁷);

R⁶ is hydrogen or halogen;

Y is oxygen, sulfur or methylene;

is a 2- to 5-membered chain of methylene units and, if desired, one or two of the following members: --O--, --S--, --CS--, --CO-- or --CH(C₁ -C₄ -alkyl)-- or --N(R¹⁴)--, in which R¹⁴ is hydrogen, C₁ -C₄ -alkyl, phenyl or benzyl;

R⁷ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₂ -C₄ -alkenyl, --COOR¹⁸ or --CO--N(R¹⁹,R²⁰);

R⁸, R⁹, R¹⁰ and R¹³ independently of one another are hydrogen, cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₂ -C₄ -alkenyl, --COOR²¹, --CO--N (R²², R²³), --N(R²²,R²³) or --N(R²⁴)--CO--R²⁵ ;

R¹¹ is cyano, halogen, --COOR²⁶, --CO--N(R²⁷,R²⁸), --N(R²⁷,R²⁸), azido, hydroxyl, C₁ -C₈ -alkoxy, C₁ -C₈ -haloalkoxy, C₃ -C₆ -alkenyloxy or (C₁ -C₄ -alkyl)carbonyloxy;

R¹² is isoxazolidinylcarbonyl, --COOR²⁹, --CO--SR²⁹, --CO--N (R³⁴) --OR²⁹, --CO--O--N═C(R³¹)--(C₁ -C₆ -alkyl), --CO--O--N═C(R³¹)--(C₁ -C₆ -alkyl), --CO--O--N═C(R³¹)--(C₁ -C₄ -alkyl) --CO--O--(C₁ -C₄ -alkyl), --CO--O--CH₂ --R¹⁴, --CO--O--C(R¹⁴)--(C₁ -C₄ -alkyl), --CO--N(R³⁴,R³⁵), --CS--N(R³⁴,R³⁵), --CO--NH--SO₂ --(C₁ -C₄ -alkyl), --CO--R³⁶, --CO--O--(C₁ -C₄ -alkyl)--C(R¹⁴)═N--O--(C₁ -C₄ -alkyl), --CO--N(R³⁴)--C(R³⁵,R³⁰)--COOR²⁹, cyclopentyliminooxycarbonyl or cyclohexyliminooxycarbonyl, in which the carbocycles may if desired carry from one to three C₁ -C₄ -alkyl radicals;

R¹⁵, R¹⁸, R²¹, R²⁶ and R²⁹ are independently of one another hydrogen, C₁ -C₈ -alkyl, C₁ -C₈ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -haloalkenyl, cyano-C₁ -C₈ -alkyl, C₃ -C₆ -alkynyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, 2-tetrahydrofuranyl-C₁ -C₈ -alkyl, 3-oxetanyl, 3-thietanyl, carboxy-C₁ -C₆ -alkyl, (C₁ -C₈ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl, cyclopropylmethyl, (1-methylthiocycloprop-1-yl)methyl, C₃ -C₉ -(α-alkylalkylidene)iminooxy-C₁ -C₆ -alkyl, (C₁ -C₄ -alkyl)carbonyl, C₁ -C₄ -alkyl which is substituted by --C(R³²)═N--O--(C₁ -C₄ -alkyl), --C(R³²)═N--O--(C₁ -C₄ -haloalkyl), --C(R³²)═N--O--(C₂ -C₆ -alkenyl), --C(R³²)═N--O--(C₂ -C₆ -haloalkenyl) or --C(R³²)═N--O--(C₁ -C₄ -alkyl)--R³⁷,

or are C₃ -C₇ -cycloalkyl or C₅ -C₇ -cycloalkenyl each of which may if desired carry from one to three C₁ -C₃ -alkyl radicals,

or are 5- or 6-membered saturated heterocyclyl or heterocyclyl-C₁ -C₆ -alkyl having in each case one oxygen, sulfur or aza ring member and, if desired, a further oxygen or sulfur ring member and/or a carbonyl or thiocarbonyl ring member, where each hydrogen atom attached to a ring member may if desired be replaced by one of the following substituents: hydroxyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, (C₁ -C₄ -alkoxy)carbonyl, (C₁ -C₄ -alkyl)carbonyloxy or (C₁ -C₄ -haloalkyl)- carbonyloxy,

or are phenyl, phenyl-C₁ -C₆ -alkyl, phenyl-C₂ -C₆ -alkenyl, phenyl-C₂ -C₆ -alkynyl or phenoxy-C₁ -C₆ -alkyl, where each phenyl ring may be unsubstituted or may carry from one to three radicals in each case selected from the group consisting of nitro, cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy and C₂ -C₆ -alkenyl,

or are 5- or 6-membered hetaryl, hetaryl-C₁ -C₆ -alkyl, hetaryl-C₂ -C₆ -alkenyl, hetaryl-C₂ -C₆ -alkynyl or (hetaryl)oxy-C₁ -C₆ -alkyl, in which each hetaryl radical contains from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom and may also if desired carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkoxy;

R¹⁶, R¹⁷, R¹⁹, R²⁰, R²², R²³, R²⁷, R²⁸, R³⁴ and R³⁵ are independently of one another hydrogen, cyano, C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl, C₂ -C₈ -alkynyl, C₁ -C₈ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, cyano-C₁ -C₄ -alkyl, carboxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₆ -alkoxy, (C₃ -C₆ -cyclo-alkyl)oxycarbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)-carbonyl-C₁ -C₄ -alkyl, (C₁ -C₄ -alkyl)carbonyl, (C₁ -C₄ -haloalkyl)carbonyl, aminocarbonyl,

or are phenyl or phenyl-C₁ -C₄ -alkyl in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl and C₂ -C₆ -alkenyl,

or are 5- or 6-membered hetaryl or hetaryl-C.sub. -C₄ -alkyl in which the hetaryl radical contains from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom and may also if desired carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkyl; or

R¹⁶ and R¹⁷ and/or R¹⁹ and R²⁰ and/or R²² and R²³ and/or R²⁷ and R²⁸ and/or R³⁴ and R³⁵ together are a propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain;

R²⁴ is hydrogen, C₁ -C₄ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or the equivalent of an agriculturally usable cation;

R²⁵ and R³⁰ are hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl,

or are C₃ -C₇ -cycloalkyl which may if desired carry from one to three radicals selected from the group consisting of halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and C₁ -C₄ -alkylthio,

or are phenyl or phenyl-C₁ -C₆ -alkyl in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkyl;

R³¹ is C₁ -C₆ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₆ -alkoxy-C₁ C₄ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-(C₁ -C₄ -alkyl), di- (C₁ -C₆ -alkoxy)carbonyl!-C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, (C₁ -C₆ -alkoxy)carbonyl, 2-furyl or phenyl which may be unsubstituted or may in turn carry from one to three radicals selected from the group consisting of halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy;

R³² is hydrogen, C₁ -C₄ -alkyl, phenyl or benzyl;

R³⁶ is hydrogen, halogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -halo-alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl;

R³⁷ is phenyl or 5- or 6-membered hetaryl having from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, where the phenyl ring and the hetaryl rings may if desired carry at each substitutable carbon atom one of the following substituents: nitro, cyano, hydroxy, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkyl.

The invention also relates to the use of these compounds as herbicides, to herbicidal compositions comprising the compounds I as active substances, to processes for producing these herbicidal compositions and to methods of combating unwanted plant growth with the compounds I.

JP 03 151 367 describes herbicidally active 1-(1-alkyl-4-halo-5-haloalkoxy-1H-pyrazol-3-yl)-4,6-dihalophenyl derivates having various substituents in position 3 of the phenyl ring, especially compounds having the following substitution pattern IIa: ##STR5## Furthermore, EP-A 443 059 teaches that 1-alkyl- and 1-haloalkyl-3(4-chloro-6-halophenyl)pyrazoles and -4-halopyrazoles which carry specific substituents in position 3 of the phenyl ring and are substituted in position 5 of the pyrazole ring by hydroxyl, mercapto, lower alkoxy, alkylthio, haloalkoxy or haloalkylthio are suitable for controlling unwanted plants.

Furthermore, JP-A 03/072 460 discloses the fact that 3-substituted phenylpyrazoles of the formula IIb ##STR6## in which R^(a) is hydrogen, halogen or cyano and R^(b) is lower alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl are herbicidally active. EP-A 447 055 discloses that 1-(lower alkyl)-3-(4-chloro-6-halophenyl)-4-halo-5-difluoromethoxypyrazoles which carry in position of the phenyl ring an alkylthiocarbonyl-, alkenylthiocarbonyl- or benzylthiocarbonyl-methoxycarbonyl group display herbicidal activity.

In JP-A 03/047 180 and JP-A 03/081 275 it is disclosed that, inter alia, pyrazole derivatives of the formulae IIc and IId ##STR7## in which R^(c) is hydrogen, methyl or allyl and

R^(d) is hydrogen, ethyl, allyl or propargyl

are suitable as herbicides.

According to JP-A 02/300 173 and JP-A 03/093 774, certain 1-alkyl-3-phenylpyrazoles which may carry on the phenyl ring from one to four halogen atoms likewise display herbicidal activity. Those mentioned in particular are 1-methyl-3-(2,4-dichlorophenyl)pyrazoles and three 1-methyl-5-chloro-3-(2-fluoro-4-chlorophenyl)-pyrazoles.

Finally, WO 92/06962 describes herbicidal 4-halo-5-haloalkyl-3-phenylpyrazoles having various substituents on the phenyl ring.

However, the herbicidal properties of the known herbicides with respect to harmful plants give only limited satisfaction.

It is an object of the present invention to provide novel herbicidally active compounds which can be used to give targeted control of unwanted plants which represents an improvement on the prior art.

We have found that this object is achieved by the substituted 3-phenylpyrazoles of the formula I. We have also found herbicidal compositions which comprise the compounds I and possess a very good herbicidal action. We have additionally found processes for producing these compositions and methods of combating unwanted plant growth with the compounds I.

With regard to the use of the substituted 3-phenylpyrazoles I as herbicides, preference is given to compounds I in which the variables are as defined below, in each case individually or in combination:

R¹ is --C(R⁸)═C(R⁷,R¹²), ##STR8## --C(R⁹,R¹⁰)--C(R⁸,R¹¹ R¹²), ##STR9## or is --C(R⁹)═C(R⁸)-phenyl in which the phenyl ring may if desired carry from one to three substituents selected from the group consisting of nitro, cyano, fluorine, chlorine, bromine, trifluoromethyl, hydroxyl, hydroxycarbonyl, C₁ -C₄ -alkoxy and C₁ -C₄ -alkoxycarbonyl;

particularly preferably --C(R⁸)═C(R⁷,R¹²) or --C(R⁹,R¹⁰)--C(R⁸,R¹¹,R¹²);

R² is trifluoromethyl, halogen or cyano; particularly preferably halogen or cyano;

R³ is C₁ -C₄ -alkyl or C₁ -C₄ -haloalkyl; particularly preferably C₁ -C₄ -alkyl;

R⁴ is C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkylthio; particularly preferably C₁ -C₄ -haloalkoxy or C₁ -C₄ -haloalkylthio;

R⁵ is nitro, halogen, --COOR¹⁵ or --CO--N(R¹⁶,R¹⁷); particularly preferably halogen or cyano;

R⁶ is hydrogen or halogen;

is a 2- to 5-membered chain of methylene units and, if desired, one or two of the following members: --O--, --S--, --N(R³³)--, --CS--, --CO-- or --CH(C₁ -C₄ -alkyl)--N(R¹⁴)--, in which R¹⁴ is hydrogen, C₁ -C₄ -alkyl, phenyl or benzyl; particularly preferably a 4- to 5-membered chain of methylene units and, if desired, one or two of the following members: --O--, --CO-- or --CH(C₁ -C₄ -alkyl)-- or --N(R¹⁴)--, in which R¹⁴ is hydrogen or C₁ -C₄ -alkyl;

R⁷ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₂ -C₄ -alkenyl, --COOR¹⁸ or --CO--N(R¹⁹,R²⁰); particularly preferably cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, --COOR¹⁸ or --CO--N(R¹⁹,R²⁰);

R⁸, R⁹, R¹⁰, R¹³ are independently of one another hydrogen, cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, --COOR²¹, stop --CO--N(R²²,R²³), --N(R²²,R²³) or --N(R²⁴)--CO--R²⁵ ; particularly preferably hydrogen;

R¹¹ is cyano, halogen, --COOR²⁶, --CO--N(R²⁷,R²⁸), --N(R²⁷,R²⁸), hydroxyl, C₁ -C₈ -alkoxy, C₁ -C₈ -haloalkoxy, C₃ -C₆ -alkenyloxy or (C₁ -C₄ -alkyl)carbonyloxy;

R¹² is isoxazolidinylcarbonyl, --COOR²⁹, --CO--SR²⁹, --CO--N(R³⁴)--OR²⁹, --CO--O--N═C(R³¹)--(C₁ -C₆ -alkyl), --CO--O--N═C(R³¹)--CO--O--(C₁ -C₆ -alkyl), --CO--O--N═C(R³¹)--(C₁ -C₄ -alkyl)--CO--O--(C₁ -C₄ -alkyl), --O--CH₂ --R¹⁴, --CO--O--C(R¹⁴)--(C₁ -C₄ -alkyl), --CO--N(R³⁴,R³⁵), --CS--N(R³⁴,R³⁵), --CO--NH--SO₂ --(C₁ -C₄ -alkyl), --CO--R³⁶, --CO--O--(C₁ -C₄ -alkyl)--C(R³³)═N--O--(C₁ -C₄ -alkyl), --CO--N(R³⁴)--C(R³⁵,R³⁰)--COOR²⁹, cyclopentyliminooxycarbonyl or cyclohexyliminooxycarbonyl, in which the carbocycles may if desired carry one to three C₁ -C₄ -alkyl radicals; particularly preferably --COOR²⁹, --CO--O--C(R¹⁴)--(C₁ -C₄ -alkyl), --CO--N(R³⁴,R³⁵) or --CO--N(R³⁴)--C(R³⁵, R³⁰)--COOR²⁹ ;

R¹⁵, R¹⁸, R²¹, R²⁶ are independently of one another C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl or C₂ -C₄ -alkenyl; particularly preferably C₁ -C₄ -alkyl;

R¹⁶, R¹⁷, R¹⁹, R²⁰, R²², R²³, R²⁷, R²⁸ are independently of one another hydrogen, cyano, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₂ -C₄ -alkynyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl, C₃ -C₈ -cycloalkyl, (C₁ -C₄ -alkyl)carbonyl, aminocarbonyl, phenyl or phenyl-C₁ -C₄ -alkyl, in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and C₁ -C₄ -haloalkyl; and are particularly preferably hydrogen, C₁ -C₄ -alkyl or (C₁ -C₄ -alkyl)carbonyl;

R²⁹ is hydrogen, C₁ -C₈ -alkyl, C₁ -C₈ -haloalkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -haloalkenyl, C₂ -C₈ -cyanoalkyl, C₃ -C₆ -alkynyl, C₂ -C₈ -alkoxyalkyl, 2-tetrahydrofuranyl-C₁ -C₈ -alkyl, 3-oxetanyl, 3-thietanyl, carboxy-C₁ -C₆ -alkyl, (C₁ -C₈ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl, cyclopropylmethyl, (1-methylthiocycloprop-1-yl)methyl, C₃ -C₉ -(α-alkylalkylidene)iminooxy-C₁ -C₆ -alkyl, C₁ -C₄ -alkyl which is substituted by --C(R³²)═N--O--(C₁ -C₄ -alkyl), --C(R³²)═N--O--(C₁ -C₄ -haloalkyl), --C(R³²)=N--O--(C₂ -C₆ -alkenyl), --C(R³²)═N--O--(C₃ -C₆ -haloalkenyl) or --C(R³²)═N--O--(C₁ -C₄ -alkyl)-R³⁷,

or is C₃ -C₇ -cycloalkyl or C₅ -C₇ -cycloalkenyl, each of which may if desired carry from one to three C₁ -C₃ -alkyl radicals, or is phenyl, phenyl-C₁ -C₆ -alkyl, phenyl-C₂ -C₆ -alkenyl, phenyl-C₂ -C₆ -alkynyl or phenoxy-C₁ -C₆ -alkyl, in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of nitro, cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy and C₂ -C₆ -alkenyl,

or is 5- or 6-membered hetaryl, hetaryl-C₁ -C₆ -alkyl, hetaryl-C₂ -C₆ -alkenyl, hetaryl-C₂ -C₆ -alkynyl or hetaryl-oxy-C₁ -C₆ -alkyl, in which the hetaryl radical contains in each case from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom and may also if desired carry on each substitutable ring atom a radical selected from the group consisting of hydroxyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio and C₁ -C₄ -haloalkoxy;

particularly preferred radicals R²⁹ are C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -alkenyl, cyano-C₁ -C₄ -alkyl, C₃ -C₆ -alkynyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl and (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl;

R³⁴ and-R³⁵ are independently of one another hydrogen, cyano, C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, cyano-C₁ -C₄ -alkyl, carboxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy, (C₃ -C₆ -cycloalkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, (C₁ -C₄ -alkyl)carbonyl, (C₁ -C₄ -haloalkyl)carbonyl, aminocarbonyl, phenyl or phenyl-C₁ -C₄ -alkyl, in which the phenyl ring may in each case be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and C₁ -C₄ -haloalkyl;

or R³⁴ and R³⁵ together are a propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain;

particularly preferred radicals R³⁴ and R³⁵ are hydrogen, cyano, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl, cyclopropyl, (C₁ -C₄ -alkyl)carbonyl or phenyl-C₁ -C₄ -alkyl, in which the phenyl ring may be unsubstituted or may carry from one to three radicals selected from the group consisting of halogen, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl and C₂ -C₆ -alkenyl, or R³⁴ and R³⁵ together are a propylene or tetramethylene chain;

R²⁴ is hydrogen, C₁ -C₄ -alkyl, C₃ -C₆ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or the equivalent of an agriculturally usable cation; particularly preferably hydrogen, C₁ -C₄ -alkyl or the equivalent of an agriculturally usable cation;

R²⁵ and R³⁰ are independently of one another hydrogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₃ -C₇ -cycloalkyl which may if desired carry one or two radicals selected from the group consisting of halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy and C₁ -C₄ -alkylthio; and are particularly preferably hydrogen or C₁ -C₄ -alkyl;

R³¹ is C₁ -C₆ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-(C₁ -C₄ -alkyl), di- (C₁ -C₄ -alkoxy)carbonyl!-C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy, (C₁ -C₄ -alkoxy)carbonyl, 2-furyl or phenyl which may be unsubstituted or may in turn carry from one to three radicals selected from the group consisting of halogen, C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy; and is preferably C₁ -C₄ -alkyl;

R³² hydrogen or C₁ -C₄ -alkyl;

R³⁶ is hydrogen, halogen, C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl; particularly preferably C₁ -C₄ -alkyl or C₁ -C₄ -haloalkyl,

and

R³⁷ is phenyl or 5- or 6-membered hetaryl having from one to three heteroatoms selected from a group consisting of one or two nitrogen atoms and one oxygen or sulfur atom, where the phenyl ring and the hetaryl rings may if desired carry on each substitutable carbon atom one of the following substituents: nitro, cyano, hydroxyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio or C₁ -C₄ -haloalkyl.

The organic moieties indicated for substituents R¹ to R³⁷ or as radicals on (hetero)aromatic structures, and also the definition halogen (halo), represent collective designations for individual members of the groups. All carbon chains, ie. all alkyl, alkylcarbonyl, alkenyl, alkynyl, haloalkyl, haloalkylcarbonyl, haloalkenyl, haloalkynyl, cyanoalkyl, phenylalkyl, carboxyalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl and alkylsulfonyl moieties and the α-alkylalkylidene moiety may be straight-chain or branched. Halogenated substituents preferably carry from 1 to 5 identical or different halogen atoms.

Specific examples are:

for halogen: fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine;

for C₁ -C₄ -alkyl and the alkyl moieties of --CO--O--N═C(R³¹)--(C₁ -C₄ -alkyl)--CO--O--(C₁ -C₄ -alkyl), --CO--O--C(R¹⁴)--(C₁ -C₄ -alkyl), --CO--NH--SO₂ --(C₁ -C₄ -alkyl), --CO--O--(C₁ -C₄ -alkyl)--C(R¹⁴)═N--O--(C₁ -C₄ -alkyl), C₁ -C₆ -alkoxy-C₁ -C₄ -alkyl, di- (C₁ -C₆ -alkoxy)carbonyl!-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, di- (C₁ -C₆ -alkoxy)carbonyl!-C₁ -C₄ -alkyl, C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl, (C₃ -C₆ -cycloalkyl)oxycarbonyl-C₁ -C₄ -alkyl (C₁ -C₄ -alkyl)carbonyloxy and C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, preferably methyl and ethyl; for C₁ -C₆ -alkyl and the C₁ -C₆ -alkyl moieties of --CO--O--N═C(R³¹)--(C₁ -C₆ -alkyl), --CO--O--N═C(R³¹)--CO--O--(C₁ -C₆ -alkyl), carboxy-C₁ -C₆ -alkyl, (C₁ -C₈ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₃ -C₉ -(α-alkyl-alkylidene)iminooxy-C₁ -C₆ -alkyl, phenoxy-C₁ -C₆ -alkyl and (hetaryl)oxy-C₁ -C₆ -alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, preferably C₁ -C₄ -alkyl as above, especially methyl and ethyl;

for C₁ -C₈ -alkyl and the alkyl moieties of 2-tetrahydro-furanyl-C₁ -C₈ -alkyl and cyano-C₁ -C₈ -alkyl: C₁ -C₆ -alkyl as above and, for example, n-heptyl, n-octyl, preferably C₁ -C₆ -alkyl, especially C₁ -C₄ -alkyl as above;

for C₂ -C₄ -alkenyl: ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl and 2-methylprop-2-en-1-yl, preferably ethenyl and allyl;

for C₂ -C₆ -alkenyl and the alkenyl moieties of phenyl-C₂ -C₆ -alkenyl and hetaryl-C₂ -C₆ -alkenyl: ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methyl-but-1-en-1-yl, 1-methyl-but-2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-1-en-2-yl, 1-ethyl-prop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-1-yl, 4-methyl-pent-2-en-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl-pent-4-en-t-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1,2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-1-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl-but-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethyl-prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl-prop-2-en-1-yl, preferably C₂ -C₄ -alkenyl as above;

for C₂ -C₈ -alkenyl: C₂ -C₆ -alkenyl as above and, for example, n-hept-2-en-1-yl, n-oct-2-en-1-yl, preferably C₂ -C₆ -alkenyl; for C₃ -C₆ -alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methyl-ethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl-but-1-en-1-yl, 2-methyl-but-1-en-1-yl, 3-methyl-but-1-en-1-yl, 1-methyl-but-2-en-1-yl, 2-methyl-but-2-en-1-yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1,1-dimethyl-prop-2-en-1-yl, 1,2-dimethyl-prop-1-en-1-yl, 1,2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-1-en-2-yl, 1-ethyl-prop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methyl-pent-1-en-1-yl, 2-methyl-pent-1-en-1-yl, 3-methyl-pent-1-en-1-yl, 4-methyl-pent-1-en-1-yl, 1-methyl-pent-2-en-1-yl, 2-methyl-pent-2-en-1-yl, 3-methyl-pent-2-en-1-yl, 4-methyl-pent-2-en-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-pent-3-en-1-yl, 4-methyl-pent-3-en-1-yl, 1-methyl-pent-4-en-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent-4-en-1-yl, 1,1-dimethyl-but-2-en-1-yl, 1,1-dimethyl-but-3-en-1-yl, 1,2-dimethyl-but-1-en-1-yl, 1-2-dimethyl-but-2-en-1-yl, 1,2-dimethyl-but-3-en-1-yl, 1,3-dimethyl-but-1-en-1-yl, 1,3-dimethyl-but-2-en-1-yl, 1,3-dimethyl-but-3-en-1-yl, 2,2-dimethyl-but-3-en-1-yl, 2,3-dimethyl-but-1-en-1-yl, 2,3-dimethyl-but-2-en-1-yl, 2,3-dimethyl-but-3-en-1-yl, 3,3-dimethyl-but-1-en-1-yl, 3,3-dimethyl--but-2-en-1-yl, 1-ethyl-but-1-en-1-yl, 1-ethyl-but-2-en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-1-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1,1,2-trimethyl-prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl, 1-ethyl-2-methyl-prop-1-en-1-yl and 1-ethyl-2-methyl-prop-2-en-1-yl, preferably C₃ - or C₄ -alkenyl;

for C₂ -C₆ -alkynyl and the alkynyl moieties of phenyl-C₂ -C₆ -alkynyl and hetaryl-C₂ -C₆ -alkynyl: ethynyl, prop-1-yn-1-yl, prop-2-yn-3-yl, n-but-1-yn-1-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-1-yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl, 4-methyl-pent-2-yn-5-yl, preferably C₂ -C₄ -alkynyl such as ethynyl, prop-1-yn-1-yl, prop-2-yn-3-yl, n-but-1-yn-1-yl, n-but-1-yn-4-yl and n-but-2-yn-1-yl;

for C₂ -C₈ -alkynyl: C₂ -C₆ -alkynyl as above and, for example, n-hept-2-yn-1-yl, n-oct-3-yn-1-yl, preferably C₂ -C₆ -alkynyl as specified above individually and as preferred;

for C₃ -C₆ -alkynyl: prop-1-yn-1-yl, prop-2-yn-3-yl, n-but-1-yn-1-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-1-yn-1-yl, 3-methyl-but-1-yn-3-yl, 3-methyl-but-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methyl-pent-1-yn-1-yl, 3-methyl-pent-1-yn-3-yl, 3-methyl-pent-1-yn-4-yl, 3-methyl-pent-1-yn-5-yl, 4-methyl-pent-1-yn-1-yl, 4-methyl-pent-2-yn-4-yl and 4-methyl-pent-2-yn-5-yl, preferably C₃ -or C₄ -alkynyl, especially ethynyl and prop-2-yn-3-yl;

for C₁ -C₄ -haloalkyl: C₁ -C₄ -alkyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-tri-chloroethyl, pentafluoroethyl, 3-chloropropyl, heptafluoropropyl, preferably trifluoromethyl and 1,2-dichloroethyl;

for C₁ -C₆ -haloalkyl: C₁ -C₆ -alkyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. C₁ -C₄ -haloalkyl as above, preferably C₁ -C₄ -haloalkyl as specified above individually and as preferred;

for C₁ -C₈ -haloalkyl: C₁ -C₈ -alkyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. for C₁ -C₄ -haloalkyl as above and for 7-chloro-hept-1-yl, preferably for C₁ -C₆ -haloalkyl as above, especially for C₁ -C₄ -haloalkyl as above;

for C₃ -C₆ -haloalkenyl: C₃ -C₆ -alkenyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. 2-chloroallyl, 3-chloroallyl, 3,3-dichloroallyl, preferably C₃ - or C₄ -haloalkenyl; for cyano-C₁ -C₈ -alkyl: cyano-C₁ -C₄ -alkyl such as cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl and 2-cyanomethyl-prop-2-yl, preferably cyano-C₁ -C₄ -alkyl, especially 2-cyanoeth-1-yl;

for phenyl-C₁ -C₄ -alkyl: benzyl, 1-phenyleth-1-yl, 2-phenyleth-1-yl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylprop-2-yl, 2-phenylprop-2-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 1-phenylbut-3-yl, 2-phenylbut-3-yl, 1-phenyl-2-methyl-prop-3-yl, 2-phenyl-2-methyl-prop-3-yl, 3-phenyl-2-methyl-prop-3-yl and 2-benzyl-prop-2-yl;

for phenyl-C₁ -C₆ -alkyl: phenyl-C₁ -C₄ -alkyl as above and, for example, 2-phenyl-hex-6-yl, preferably phenyl-C₁ -C₄ -alkyl as above;

for hetaryl-C₁ -C₆ -alkyl: hetaryl-C₁ -C₄ -alkyl such as hetarylmethyl, 1-(hetaryl)eth-1-yl, 2-(hetaryl)eth-1-yl, 1-(hetaryl)prop-1-yl, 2-(hetaryl)prop-1-yl, 3-(hetaryl)-prop-1-yl, 1-(hetaryl)prop-2-yl, 2-(hetaryl)prop-2-yl, 1-(hetaryl)but-1-yl, 2-(hetaryl)but-1-yl, 3-(hetaryl)-but-1-yl, 4-(hetaryl)but-1-yl, 1-(hetaryl)but-2-yl, 2-(hetaryl)but-2-yl, 1-(hetaryl)but-3-yl, 2-(hetaryl)-but-3-yl, 1-(hetaryl)-2-methyl-prop-3-yl, 2-(hetaryl)-2-methyl-prop-3-yl, 3-(hetaryl)-2-methyl-prop-3-yl and 2-(hetarylmethyl)-prop-2-yl, preferably hetaryl-C₁ -C₄ -alkyl;

for carboxy-C₁ -C₄ -alkyl: carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, 1-carboxyprop-1-yl, 2-carboxyprop-1-yl, 3-carboxyprop-1-yl, 1-carboxybut-1-yl, 2-carboxybut-1-yl, 3-carboxybut-1-yl, 4-carboxybut-1-yl, 1-carboxybut-2-yl, 2-carboxybut-2-yl, 3-carboxybut-2-yl, 3-carboxybut-2-yl, 4-carboxybut-2-yl, 1-(carboxymethyl)-eth-1-yl, 1-(carboxymethyl)-1-(methyl)-eth-1-yl and 1-(carboxymethyl)-prop-1-yl, preferably carboxymethyl and carboxyethyl;

for carboxy-C₁ -C₆ -alkyl: carboxy-C₁ -C₄ -alkyl as above and, for example, 5-carboxypent-1-yl, preferably carboxy-C₁ -C₄ -alkyl;

for C₁ -C₄ -alkoxy and the alkoxy moieties of C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl and C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, preferably methoxy, ethoxy and 1-methylethoxy;

for the alkoxy moiety C₁ -C₆ -alkoxy-C₁ -C₄ -alkyl: C₁ -C₄ -alkoxy as above and n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methyl-pentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, preferably C₁ -C₄ -alkoxy, especially methoxy, ethoxy and 1-methylethoxy;

for C₁ -C₄ -alkylthio and the alkylthio moiety of C₁ -C₄ -alkyl-thio-C₁ -C₄ -alkyl: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methyl-propylthio and 1,1-dimethylethylthio, preferably methylthio, ethylthio and 1-methylethylthio;

for C₁ -C₆ -alkylthio: C₁ -C₄ -alkylthio as above and n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, preferably methylthio, ethylthio and 1-methylethylthio;

for (C₁ -C₄ -alkyl)carbonyl: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl and 1,1-dimethylethylcarbonyl;

for (C₁ -C₄ -haloalkyl)carbonyl: (C₁ -C₄ -alkyl)carbonyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethylcarbonyl, dichloromethylcarbonyl, trichloromethylcarbonyl, fluoromethylcarbonyl, difluoromethylcarbonyl, trifluoromethylcarbonyl, chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 1-fluoroethylcarbonyl, 2-fluoroethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 3-chloropropylcarbonyl and heptafluoropropylcarbonyl; for (C₁ -C₄ -alkoxy)carbonyl and the alkoxycarbonyl moieties of (C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₆ -alkyl and C₁ -C₄ -alkoxy-(C₁ -C₄ -alkoxy)carbonyl-C₁ -C₄ -alkyl: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl and 1,1-dimethylethoxycarbonyl, preferably methoxycarbonyl, ethoxycarbonyl and 1-methylethoxycarbonyl;

for (C₁ -C₆ -alkoxy)carbonyl and the alkoxycarbonyl moieties of (C₁ -C₆ -alkoxy)carbonyl-C₁ -C₄ -alkyl and di- (C₁ -C₆ -alkoxy)-carbonyl!-C₁ -C₄ -alkyl: (C₁ -C₄ -alkoxy)carbonyl as above and n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl and 1-ethyl-2-methylpropoxycarbonyl, preferably (C₁ -C₄ -alkoxy)carbonyl, especially methoxycarbonyl, ethoxycarbonyl and 1-methylethoxycarbonyl;

for the alkoxycarbonyl moiety of (C₁ -C₈ -alkoxy)carbonyl-C₁ -C₆ -alkyl: (C₁ -C₆ -alkoxy)carbonyl as above and, for example, n-heptoxycarbonyl, n-octoxycarbonyl, preferably (C₁ -C₆ -alkoxy)carbonyl, especially (C₁ -C₄ -alkoxy)carbonyl;

for C₁ -C₄ -alkylsulfinyl: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl and 1,1-dimethylethylsulfinyl, preferably methylsulfinyl and ethylsulfinyl;

for C₁ -C₄ -haloalkylsulfinyl: C₁ -C₄ -alkylsulfinyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethylsulfinyl, dichloromethylsulfinyl, trichloromethylsulfinyl, fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3-chloropropylsulfinyl and heptafluoropropylsulfinyl, preferably trifluoromethylsulfinyl;

for C₁ -C₄ -alkylsulfonyl and the alkylsulfonyl moiety of C₁ -C₄ -alkylsulfonyl-C₁ -C₄ -alkyl: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl, preferably methylsulfonyl and ethylsulfonyl;

for C₁ -C₄ -haloalkylsulfonyl: C₁ -C₄ -alkylsulfonyl as above which is partially or completely substituted by fluorine, chlorine and/or bromine, ie. eg. chloromethylsulfonyl, dichloromethylsulfonyl, trichloromethylsulfonyl, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 3-chloropropylsulfonyl and heptafluoropropylsulfonyl;

for the C₃ -C₉ -(α-alkylalkylidene) moiety of C₃ -C₉ -(α-alkyl-alkylidene)iminooxy-C₁ -C₆ -alkyl: α-methylethylidene, α-methylpropylidene, α-ethylpropylidene, especially α-methylethylidene;

for C₃ -C₆ -cycloalkyl and the cycloalkyl moiety of (C₃ -C₆ -cycloalkyl)oxycarbonyl-C₁ -C₄ -alkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, preferably cyclopropyl and cyclopentyl;

for C₃ -C₇ -cycloalkyl: C₃ -C₆ -cycloalkyl as above and cycloheptyl, preferably cyclopropyl and cyclopentyl;

for C₃ -C₈ -cycloalkyl: C₃ -C₆ -cycloalkyl as above and cycloheptyl and cyclooctyl, preferably cyclopropyl, cyclopentyl and cyclohexyl;

for C₅ -C₇ -cycloalkenyl: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, cyclohept-2-enyl, cyclohept-3-enyl and cyclohept-4-enyl, preferably cyclo-pent-1-enyl;

for 5- or 6-membered hetaryl and the hetaryl moieties of hetaryl-C₁ -C₄ -alkyl, hetaryl-C₁ -C₆ -alkyl, hetaryl-C₂ -C₆ -alkenyl, hetaryl-C₂ -C₆ -alkynyl and (hetaryl)oxy-C₁ -C₆ -alkyl: eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, preferably 3-pyrazolyl, 2-pyridinyl and 2-thienyl;

for 5- or 6-membered heterocyclyl and the heterocyclyl moiety of heterocyclyl-C₁ -C₆ -alkyl:

eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-dithiolan-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-2-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, 1,4-thioxan-2-yl, 1,4-thioxan-3-yl, 1,4-dithian-2-yl, 1,3-dithian-2-yl, 1,3-dithian-5-yl, thiomorpholin-4-yl.

Cations which are suitable as the agriculturally usable cations are in particular those which do not have an adverse effect on the herbicidal action of the compounds I, especially the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion which may, if desired, carry from one to three C₁ -C₄ -alkyl and/or hydroxy-C₁ -C₄ -alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl-(2-hydroxyethyl)ammonium, and also phosphonium ions, sulfonium ions, preferably tri-(C₁ -C₄ -alkyl)sulfonium, and sulfoxonium ions, preferably tri-(C₁ -C₄ -alkyl)-sulfoxonium.

The 3-phenylpyrazole derivatives of the formula I can be obtained in a variety of ways, in particular by one of the following methods:

A) reaction of a β-ketocarboxylic acid derivative III with hydrazine or a hydrazine derivative in an inert solvent (cf. eg. JP-A 04/225 937 and JP-A 03/072 460) and alkylation of the product IV: ##STR10## L¹ is a conventional leaving group such as halogen, --O--SO₂ CH₃, --O--SO₂ CF₃, --O--SO₂ C₄ F₉ or --O--SO₂ (p-CH₃ -C₆ H₄);

R³⁸ is preferably C₁ -C₄ -alkoxy, C₁ -C₄ -alkylcarbonyloxy or halogen and; R¹, is as defined for R¹ and additionally hydrogen, nitro, amino, alkyl, haloalkyl, hydroxyl or L², where L² is a conventional leaving group, for example as mentioned for L¹.

The solvent may be aprotic or protic. Suitable examples are organic acids such as acetic acid, hydrocarbons, halogenated hydrocarbons, ethers such as ethylene glycol dimethyl ether, alcohols such as methanol or ethanol, and sulfoxides. However, working in the absence of solvents is also possible.

The reaction temperature depends primarily on the melting point of the solvent or the compound III and on the boiling point of the reaction mixture. It is preferred to work at from about 60° to 120° C.

In general from about 0.95 to 5 times the molar amount, advantageously from 1 to 1.4 times the amount, of hydrazine or hydrazine derivative are employed, based on the β-ketocarboxylic acid derivate III.

The quantity of alkylating agent L¹ -(C₁ -C₄ -alkyl) or L¹ -(C₁ -C₄ -haloalkyl) is usually likewise from 0.95 to 5 times the molar amount, based on the intermediate IV.

With regard to the preferred radicals R³ on the 3-phenylpyrazoles I, particularly preferred hydrazine derivatives are those which carry an alkyl group.

Alkylation is normally carried out with the halide, preferably with the chloride or bromide, or with the sulfate of an alkane or haloalkane, if desired in the presence of an organic base, eg. a trialkylamine or pyridine, or of an inorganic base, eg. an alkali metal carbonate.

The alkylation is expediently carried out in an inert organic solvent, eg. in an aliphatic or cyclic ether such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane, in an aliphatic ketone such as acetone, in an amide such as dimethylformamide, in a sulfoxide such as dimethyl sulfoxide or in a mixture of one of these solvents and water.

The reaction can generally be performed at from 0° C. to the boiling temperature of the reaction mixture. It is preferred to work at from about 20° to 80° C.

When Z is S the product can be oxidized in a manner known per se to the sulfoxide or sulfone (cf. eg. Houben-Weyl, Methoden der Organischen Chemie Methods of Organic Chemistry!, Vol. 9, 4th Edition 1955, pp. 211 and 227; Org. Synth. Coll. Vol. V, 791): ##STR11## B) Halogenation of compounds I' where R⁵ is hydrogen: ##STR12##

The reaction can be carried out in an inert solvent or diluent or without solvent.

Examples of suitable solvents are organic acids, inorganic acids, hydrocarbons, halogenated hydrocarbons, aromatic hydrocarbons, ethers, sulfides, sulfoxides and sulfones. Examples of suitable halogenating agents are chlorine, bromine, N-bromosuccinimides, N-chlorosuccinimides or sulfuryl chloride. Depending on the starting compound and halogenating agent the addition of a free-radical initiator, for example an organic peroxide such as dibenzoyl peroxide or an azo compound such as azobisisobutyronitrile, or irradiation with light, may have an advantageous effect on the course of the reaction.

The quantity of halogenating agent is not critical. Both substoichiometric quantities and large excesses of halogenating agent, based on the compound I to be halogenated where R⁵ is hydrogen, are possible.

When a free-radical initiator is used, a catalytic amount is generally sufficient.

The reaction is normally carried out at from -100° to 200° C., preferably at from 10° to 100° C. or at the boiling point of the reaction mixture.

C) Olefinization of 3-(formylphenyl)pyrazoles V to compounds I in which R¹ is unsaturated: ##STR13##

Olefinization is carried out preferably by the method of Wittig or one of its modifications, with suitable reactants being phosphorylides, phosphonium salts and phosphonates, or by aldol condensation.

When using a phosphonium salt or a phosphonate it is advisable to work in the presence of a base, among which the following are particularly suitable: alkali metal alkyls such as n-butyllithium, alkali metal hydrides and alcoholates such as sodium hydride, sodium ethanolate and potassium tert-butanolate, and alkali metal hydroxides and alkaline earth metal hydroxides such as calcium hydroxide.

For complete reaction, all of the reactants are employed in an approximately stoichiometric ratio; however, it is preferred to use an excess of phosphorus compound and/or base of up to about 10 mol %, based on V.

The reaction temperature is generally from -40° to 150° C. A further possibility for preparing compounds I is first of all to convert the 3-(formylphenyl)pyrazoles V in a manner known per se into the corresponding ketones VI ##STR14## in which R⁷ ' is as defined for R⁷ with the exception of halogen (for example reacting V with a suitable salt MR⁷ ' in which M is eg. lithium or magnesium and then oxidizing the alcohol formed) and subsequently subjecting the products to the Wittig reaction.

The phosphonium salts, phosphonates or phosphorylides required as reactants are known or can be prepared in a manner known per se {cf. eg. Houben-Weyl, Methoden d. Org. Chemie {Methods of Organic Chemistry!, Vol. E 1, p. 636 ff and Vol. E 2, p. 345 ff, Georg Thieme Verlag Stuttgart 1982; Chem. Ber. 95, (1962) 3993}.

The aldol condensation can be carried out in a manner known per se (see e.g. Synthesis 1978, 56; Synthesis 1978, 58; Synth. Commun. 18(7), (1988) 717, Synthesis 1986, 1026; Chem. Rev. 1993, 1449).

The 3-(formylphenyl)pyrazoles V can be obtained, for example, by halogenation of 3-(methylphenyl)pyrazoles VII followed by acid hydrolysis of 3-(dihalomethylphenyl)pyrazoles VIIIa or oxidation of 3-(halomethylphenyl)pyrazoles VIIIb: ##STR15##

Hal=halogen, preferably chlorine or bromine.

With respect to the solvents, proportions and reaction temperature for the halogenation, reference is made to the comments under method B). Photochemical halogenation can also be used to carry out halogenation at R³ of compounds VIIIa where R³ is methyl (VIIIa, R³ =CH₂ R³⁹, R³⁹ =halogen): ##STR16## R³⁹ is halogen or C₁ -C₄ -alkoxy.

The reaction products may then if desired be converted in a manner known per se using oxygen nucleophiles or halogen nucleophiles to compounds VIIIa (R³ =CH₂ R³⁹, R³⁹ =halogen or C₁ -C₄ -alkoxy).

The hydrolysis of VIIIa is preferably carried out without solvents in an acid such as hydrochloric acid, sulfuric acid or acetic acid, especially concentrated sulfuric acid, or in a mixture of acetic acid and water (eg. 3:1).

The reaction temperature is normally from 0° to 120° C.

The reaction products can generally be worked up in a manner known per se.

The oxidation of the compounds VIIIb can be carried out, for example, by the method of Kornblum (in this respect see, in particular, pages 179 to 181 of "Methods for the Oxidation of Organic Compounds" by Alan H. Haines, Academic Press 1988, in the series "Best Synthetic Methods").

One example of a suitable solvent is dimethyl sulfoxide.

Further possibilities for preparing different compounds I from 3-(formylphenyl)pyrazoles V include the aldol condensation, which is known per se (suitable conditions for this can be found in, for example, Nielsen, Org. React. 16, (1968) 1 ff), and condensation reactions according to Knoevenagel or Perkin. Examples of suitable conditions are described in Org. React. 15, (1967) 204 ff {Knoevenagel} and Johnson, Org. React. 1, (1942) 210 ff {nach Perkin}.

D) Diazotization of anilines IX in a manner known per se and arylation of the resulting diazonium compounds by the method of Meerwein {see eg. C. S. Rondestvedt, Org. React. 11, (1960) pp. 189-260 and, in particular, H. P. Doyle, B. Siegfried. R. C. Elliot, J. F. Dellaria, J. Org. Chem. 42, (1977) 2431}: ##STR17## The diazonium salt can be obtained advantageously in a manner known per se by reacting an aniline IX in an aqueous acid solution, for example in hydrochloric acid, hydrobromic acid or sulfuric acid, with a nitrite such as sodium nitrite or potassium nitrite.

The reaction can also be carried out, however, without water, for example in glacial acetic acid which contains hydrogen chloride, in absolute alcohol, in dioxane or tetrahydrofuran, in acetonitrile or in acetone, in this case reacting the aniline IX with a nitrous ester such as tert-butyl nitrite or isopentyl nitrite.

The subsequent reaction of the diazonium salt with an olefin or alkine in the presence of a copper salt, preferably a copper halide such as copper(I) chloride, copper(II) chloride, copper (I) bromide or copper(II) bromide, by the method of Meerwein can be carried out, for example, in water, in a ketone such as acetone, diethyl ketone or methyl ethyl ketone, in a nitrile such as acetonitrile, in an ether such as dioxane or tetrahydrofuran, or in an alcohol such as methanol or ethanol.

Diazotization and arylation can be carried out at from -30 to ±50° C. The components of the diazotization reaction are usually employed in an approximately stoichiometric ratio, although an excess of one or other component may be advantageous.

In general the olefins or alkines to be arylated are employed in a large excess; however, it is also possible to use only a slight excess, an equivalent amount or a substoichiometric amount.

The copper halide is conventionally employed in an approximately stoichiometric quantity based on the diazonium salt or, if it is not isolated, on the aniline IX, although an excess or substoichiometric amount is also possible.

Diazotization and arylation can also be undertaken in one step. In this case diazotization is carried out in the presence of the olefin or alkine component and of the copper halide.

The anilines IX can in turn be obtained by reduction of the corresponding nitro compounds X: ##STR18##

The reduction can be carried out with a metal such as iron, zinc or tin under acidic reaction conditions or with a complex hydride such as lithium aluminum hydride or sodium borohydride, with examples of suitable solvents--depending on the reducing agent chosen--being water, alcohols such as methanol, ethanol or isopropanol, or ethers such as diethyl ether, methyl tert-butyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether.

When carrying out reduction with a metal, it is preferred to work without solvent in an inorganic acid, especially concentrated or dilute hydrochloric acid, or in an organic acid such as acetic acid. However, it is also possible to add an inert solvent, for example one of those mentioned above, to the acid.

The starting compound X and the reducing agent are advantageously employed in approximately equimolar quantities; however, in order to optimize the course of the reaction it may be advantageous to employ one of the two components in excess, up to about 10 times the molar amount.

The quantity of acid is not critical. In order to maximize reduction of the starting compound it is advantageous to use an at least equivalent quantity of acid.

The reaction temperature is in general from -30 to 200° C., preferably from 0° to 80° C.

The reaction mixture is usually worked up by diluting it with water and isolating the product by filtration, crystallization or extraction with a solvent which is substantially immiscible with water, for example with ethyl acetate, diethyl ether or methylene chloride. Subsequently the product can if desired be purified in a conventional manner.

The nitro group of the nitro compounds X can also be hydrogenated catalytically using hydrogen.

Catalysts suitable for this purpose are, for example, Raney nickel, palladium on charcoal, palladium oxide, platinum and platinum oxide, with a quantity of catalyst of from 0.05 to 10.0 mol %, based on the compound to be reduced, generally being sufficient.

The reaction is carried out either without solvent or in an inert solvent or diluent, for example in acetic acid, in a mixture of acetic acid and water, or in ethyl acetate, ethanol or toluene.

After the catalyst has been separated off the reaction solution can be worked up in a conventional manner to give the product.

Hydrogenation can be carried out at atmospheric pressure or under superatmospheric pressure.

The nitro compounds X are in turn accessible, for example, by nitration of phenylpyrazoles XI: ##STR19##

Examples of suitable nitrating reagents are nitric acid at various concentrations, including concentrated and fuming nitric acid, mixtures of sulfuric acid and nitric acid, acetyl nitrates and alkyl nitrates.

The reaction can be carried out either without solvent in an excess of the nitrating reagent or in an inert solvent or diluent, examples of suitable such solvents being water, mineral acids, organic acids, chlorinated hydrocarbons such as methylene chloride, anhydrides such as acetic anhydride, and mixtures of these solvents.

Starting compound XI and nitrating reagent are advantageously employed in approximately equimolar quantities: in order to optimize the conversion of the compound to be nitrated, however, it may be advantageous to use the nitrating reagent in an excess, up to about 10 times the molar quantity. When the reaction is carried out without solvent in the nitrating reagent, the latter is used in an even larger excess.

The reaction is generally carried out from -100° to 200° C., preferably at from -30° to 50° C.

The reaction mixture can be worked up in a known manner, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction.

E) Reaction of phenyl triflates XIII, which are obtainable in turn from phenols XII, with Grignard compounds or olefins: ##STR20## From the phenyl triflates XIII it is possible, in a manner known per se - for example by alkylation (see eg. J. Org. Chem.57, (1992) 4066-4068 and the literature cited there-in)--to prepare compounds I in which R¹ is a substituted or unsubstituted alkyl radical.

Compounds I in which R¹ is an unsaturated radical can be obtained from the phenyl triflates XIII with suitable palladium catalysis {see eg. Heterocycles 26, (1987) 355-358 and the literature cited therein under Lit. 1}.

F) Derivatization of the substituents R¹

F1) Hydrogenation of double bonds in a manner known per se:

Examples of suitable reducing agents are elemental metals such as iron, tin and zinc, hydrogen in the presence of appropriate catalysts such as palladium on charcoal, platinum on charcoal and Raney nickel, complex metal hydrides such as lithium aluminum hydride and sodium borohydride, if desired in the presence of one of the abovementioned catalysts.

Depending on the reducing agent used, examples of suitable solvents are acids such as acetic acid and propionic acid, alcohols such as methanol and ethanol, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, or aromatic compounds such as benzene and toluene. Mixtures of the solvents mentioned can also be used.

The reactions can be carried out at from -100° C. to the boiling temperature of the respective reaction mixture.

The starting materials are commonly employed in an approximately stoichiometric ratio, although in order to optimize the conversion of the compound I to be derivatized it may be advantageous to employ this compound in a substoichiometric quantity.

F2) Substitution of a halogen atom on substituent R¹, preferably a chlorine or bromine atom, by a nitrogen, oxygen or carbon nucleophile in a manner known per se:

Especially with regard to the reaction of compounds I in which the substituent R¹ carries, in addition to the halogen atom, a carboxyl group and also two further substituents on the same carbon atom, the presence of a nickel catalyst has proven to be particularly advantageous.

Depending on the reactants, examples of suitable solvents are aprotic solvents such as acetone, diethyl ketone, methyl ethyl ketone, dimethylformamide, diethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane and chlorinated hydrocarbons, for example methylene chloride or chloroform. Mixtures of the solvents mentioned are also suitable.

The reactions are generally carried out at from -30° C. to the boiling temperature of the respective solvent or solvent mixture.

The starting materials are conventionally reacted in an approximately stoichiometric ratio, although in order to optimize the conversion of the compound I to be derivatized it may be advantageous to employ this compound in a substoichiometric quantity.

F3) Conversion of compounds I in which the radical R¹ contains a carboxylic ester, to carboxylic acids and derivatives thereof in a manner known per se: ##STR21## 'R⁴⁰ here is preferably --C(R⁸)=C(R⁷)--, ##STR22## --C(R⁹,R¹⁰)--C(R⁸,R¹¹)--, --C(R⁹,R¹⁰)--C(R⁹,R¹⁰)-- or --C(R⁹,R¹⁰)--C(R⁸,phenyl)--.

R⁴¹ is in particular OR²⁹, Halogen, N(R³⁴,R³⁵), SR²⁹, N(R³⁴)--OR²⁹.

Thus, for example, esters (R⁴¹ =OR²⁹) can be hydrolyzed to carboxylic acids (R⁴¹ =OH) (see eg. Houben-Weyl, Methoden der Organischen Chemie Methods of Organic Chemistry!, Vol. 8, Georg Thieme Verlag, Stuttgart, 1952, p. 418ff.) from which the carbonyl halides (R⁴¹ =C₁) are accessible (Houben-Weyl, Methoden der Organischen Chemie Methods of Organic Chemistry!, Vol. 8, Georg Thieme Verlag Stuttgart, 1952, p. 471ff.).

Carboxylic acids or their halides (R⁴¹ =OH, Cl) can in turn be converted to carboxamides (R⁴¹ =N(R³⁴,R³⁵), N(R³⁴)--OR²⁹), carboxylic esters (R⁴¹ =OR²⁹) or thioesters (R⁴¹ =SR²⁹) (see eg. Houben-Weyl, Methoden der Organischen Chemie Methods of Organic Chemistry!, Georg Thieme Verlag, Vol. 8, 4th Edition, 1952, p. 516 ff; Vol. 9, 4th Edition 1955, p. 753ff; Vol. E5, supplementary and subsequent volume to the 4th Edition, 1985, p. 941ff.).

F4) Reaction of compounds I in which R¹ is --C(R⁸)═C(R⁷,R¹²) to give compounds I

where R¹ = ##STR23## in a manner known per se (see eg. Houben-Weyl, Methoden der Organischen Chemie {Methods of Organic Chemistry!, Georg Thieme Verlag, Stuttgart, Vol. 6/3, 4th Edition 1965, p. 385ff; Vol. 9, 4th Edition 1955, p. 153ff; Vol 4/3, 4th Edition 1942, p. 32ff.).

G) Nucleophilic cyanide substitution of compounds I where R¹ =NO2 and R² is fluorine: ##STR24##

Suitable cyanide sources MCN are in general any desired cyanide salts of metallic or organic cations, preferably alkali metal cyanides or tetraalkylammonium cyanides.

The reaction is carried out in a polar aprotic solvent at between the melting and boiling points of the latter, preferably in dimethyl sulfoxide, N,N-dimethylformamide or sulfolane at from 0° to 100° C.

It-is preferred to use a slight molar excess of the cyanide MCN based on the starting compound. However, in order to optimize the conversion it may be advantageous to use a large excess of MCN, up to about five times the molar quantity.

The reaction mixture can be worked up in a known manner, for instance by diluting the reaction mixture with water and then isolating the product by filtration, crystallization or solvent extraction.

Unless stated otherwise, the reactions described above are advantageously carried out under atmospheric pressure or under the autogenous pressure of the respective reaction mixture.

The substituted 3-phenylpyrazoles I may in the course of their preparation be obtained as isomer mixtures which, however, may if desired be separated into pure isomers by the methods which are conventional for this purpose, such as crystallization or chromatography, including chromatography on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.

Substituted 3-phenylpyrazoles I in which R⁸, R⁹, R¹⁰ or R¹³ is a radical --N(R²⁴)--CO--R²⁵ and R²⁴ is an alkali metal can be obtained by treating compounds I where R²⁴ is hydrogen, for example

with sodium hydroxide or potassium hydroxide in aqueous solution or in an organic solvent such as methanol, ethanol, acetone or toluene, or

with sodium hydride in an organic solvent such as dimethylformamide.

Salt formation normally takes place at a sufficient speed even at about 20° C.

The salt can be isolated by, for example, precipitation with a suitable inert solvent or by evaporation of the solvent.

Substituted 3-phenylpyrazoles I in which R⁸, R⁹, R¹⁰ or R¹³ is the radical --N(R²⁴)--CO--R²⁵ and R²⁴ is an agriculturally usable cation which does not belong to the group of alkali metals can be prepared conventionally by salt exchange of the corresponding compound I where R²⁴ is an alkali metal ion.

Compounds I in which R²⁴ is, for example, a manganese, copper, zinc, iron, calcium, magnesium or barium ion can be prepared from the compounds I where R²⁴ is sodium in a conventional manner, as can compounds I where R²⁴ is an ammonium or phosphonium using ammonia, phosphonium hydroxides, sulfonium hydroxides or sulfoxonium hydroxides.

Both as isomer mixtures and in the form of the pure isomers, the substituted 3-phenylpyrazoles I and salts thereof are suitable as herbicides. In crops such as wheat, rice, maize, soybean and cotton they are able to provide very effective control of broad-leaved weeds and grass weeds without noticeably damaging the crop plants. This effect occurs especially at low application rates.

Depending on the particular application method, the compounds I or herbicidal compositions comprising them can additionally be employed in a further number of crop plants in order to eliminate unwanted plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spp. altissima, Beta vulgaris spp. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spp., Manihot esculenta, Medicago sativa, Musa spp., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spp., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Moreover, the compounds I can also be employed in crops which have been rendered substantially resistant to the action of I by breeding and/or by employment of methods of genetic manipulation.

The compounds I and/or the herbicidal compositions comprising them can be applied, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting compositions, broadcasting compositions or granules, by spraying, atomizing, dusting, broadcasting or watering. The application forms depend on the intended uses; they should in each case if possible guarantee very fine dispersion of the active compounds according to the invention.

Suitable inert auxiliaries for the production of directly sprayable solutions, emulsions, pastes or oil dispersions are essentially: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, and also coaltar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, eg. amines such as N-methylpyrrolidone, and water.

Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by addition of water. For the production of emulsions, pastes or oil dispersions, the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, concentrates consisting of active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil can also be prepared, which are suitable for dilution with water.

Suitable surface-active substances are the alkali metal, alkaline earth metal or ammonium salts of aromatic sulfonic acids, eg. lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl and tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders; broadcasting and dusting compositions can be produced by mixing or conjoint grinding of the active substances with a solid carrier.

Granules, eg. coated, impregnated and homogeneous granules, can be produced by binding the active compounds to solid carriers. Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal meal, tree bark meal, sawdust, nutshell meal, cellulose powders or other solid carriers.

The concentrations of the active compounds I in the ready-to-use preparations can be varied within wide ranges, for example from 0.01 to 95% by weight, preferably from 0.5 to 90% by weight. The active compounds are in this case employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

The following formulation examples elucidate the production of such formulations:

I. 20 parts by weight of the compound No. Ia.002 are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of from 8 to 10 mol of ethylene oxide with 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. Fine dispersion of the mixture in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active compound.

II. 20 parts by weight of the compound No. Ia.003 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. Fine dispersion of the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active compound.

III. 20 parts by weight of the active compound No. Ia.020 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210° to 280° C. and 10 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. Fine dispersion of the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound No. Ia.055 are mixed thoroughly with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel and the mixture is ground in a hammer mill. Fine dispersion of the mixture in 20,000 parts by weight of water gives a spray formulation which contains 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound No. Ia.002 are mixed with 97 parts by weight of finely divided kaolin. In this way a dusting composition is obtained which contains 3% by weight of the active compound.

VI. 20 parts by weight of the active compound No. Ia.003 are mixed intimately with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol-urea-formaldehyde condensation product and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

The active compounds I and/or the herbicidal compositions can be applied pre-emergence or post-emergence. If the active compounds are less tolerable to certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of the spray equipment in such a way that the leaves of the sensitive crop plants are where possible unaffected, while the active compounds reach the leaves of unwanted plants growing under them or the uncovered soil surface (post-directed, lay-by).

The application rates of active compound are, depending on the objective of control, the time of year, the target plants and the stage of growth, from 0.001 to 3.0 kg, preferably from 0.01 to 1 kg/ha of active substance (a.s.).

In order to broaden the spectrum of action and to achieve synergistic effects, the substituted 3-phenylpyrazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, suitable cocomponents are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiocarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives which carry in position 2, for example, a carboxyl or carbimino group, quinolinecarboxylic derivatives, imidazolinones, sulfonamides, sulfonylureas, aryloxy- and hetaryloxyphenoxypropionic acids, and their salts, esters and amides, et cetera.

In addition it may be of use to mix the compounds I, alone or in combination with other herbicides, additionally with further plant protection compositions and to apply them together, for example with pesticides, fungicides or bactericides intended for combating organisms which harm plants. Also of interest is the possibility of mixing them with mineral salt solutions which are employed to eliminate nutritional and trace element deficiencies. Nonphytotoxic oils and oil concentrates can also be added.

PREPARATION EXAMPLES Example 1

Methyl 2-bromo-3-(2,4-dichloro-5- 4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl!phenyl)propenoate (Ib.006)

2.9 g (6.9 mol) of methoxycarbonylbromomethylenetriphenylphosphorane were added to a solution of 2.2 g (6.2 mmol) of 4-chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 100 ml of ethanol. The mixture was stirred at 25° C. for 4 hours and then the solvent was removed under reduced pressure. The residuewas taken up in toluene and this mixture was filtered over silica gel. Concentration by evaporation of the solvent under reduced pressure gave 1.1 g of product.

¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=3.85 (s,3H), 3.95 (s,3H), 6.74 (t,1H), 7.62 (s,1H), 8.02 (s,1H), 8.32 (s,1H).

Preparation of the precursors:

Example 2

Ethyl 4-chlorobenzoylacetate

200 g (1.29 mol) of 4-chloroacetophenone (dissolved in 500 ml of diethyl carbonate) were added dropwise at 60° C. to a mixture of 296.4 g (2.59 mol) of potassium tert-butylate and 2.25 1 of diethyl carbonate. Thesuspension, which could be stirred with difficulty, was stirred at 60° C. for 3 h and then introduced into 2.7 1 of 10% strength sulfuric acid. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate and concentration in vacuo gave the crude product, which was purified further by distillation (b.p. 130° C., 0.4 mbar). Yield: 268 g.

Example 3

Ethyl 2,4-dichloro-5-methylbenzoylacetate

Example 2 was repeated using 148 g of 2,4-dichloro-5-methylacetophenone instead of 4-chloroacetophenone. Yield: 80.4 g; b.p. (0.5 mbar): 170° C.

Example 4

3-(4-Chlorophenyl)-1-methyl-2-pyrazolin-5-one

71.2 g (1.55 mol) of methylhydrazine were added dropwise over the course of40 minutes to a suspension of 267 g (1.19 mol) of ethyl 4-chlorobenzoylacetate in 1.5 1 of acetic acid, the temperature rising to 50° C. The reaction solution was stirred at 100° C. for 2 hours and cooled, and then about 1.5 1 each of ether and water were added.The precipitate formed (66.5 g) was filtered off and washed with petroleum ether/ether (1:1). The organic phase was washed four times with saturated sodium hydrogen carbonate solution and concentrated, and the residue was taken up in water. Once again the precipitate formed was filtered off and washed with petroleum ether/ether (1:1). Overall yield: 171 g; m.p. 189° C.

Example 5

3-(2,4-Dichloro-5-methylphenyl)-1-methyl-2-pyrazolin-5-one

13.5 g (292 mol) of methylhydrazine were added slowly to 80.4 g (292 mmol) of ethyl 2,4-dichloro-5-methylbenzoylacetate in 300 m of diethylene glycoldimethyl ether. The reaction solution was heated at 100° C. for 4 hours and then stirred into 11 of ice-water. The precipitate formed was filtered off, washed with a little-methylene chloride and dried. Yield: 38.8 g; m.p. 196°-198° C.;

1H-NMR (270 MHz, in d6-dimethyl sulfoxide): 6 ppm!=2.32 (s,3H), 3.60 (s,3H), 5.89 (s,1H), 7.58 (s,1H), 7.76 (s,1H), 11.12 (s,1H).

Example 6

3-(4-Chlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

A solution of 162 g (4.0 mol) of sodium hydroxide in l 1 of water was addedto a solution of 169.1 g (0,811 mol) of 3-(4-chlorophenyl)-1-methyl-2-pyrazolin-5-one in 2.5 1 of dioxane. Chlorodifluoromethane (about 175 g) was passed in over the course of 5 hours at 60°-65° C., after which the reaction solution was stirred into 1.5 1 of water. Extraction three times with methyl tertbutyl ether, followed by drying of the organic phase and removal of the solvent in vacuo, gave the crude product, which was purified further by chromatography on silica gel (hexane/ethyl acetate 7:3). Yield: 142.9 g; 1H-NMR (400 MHz, in CDCl₃): δ ppm!=7.60 (d,2H), 7.28 (d,2H), 6.54 (t,1H), 6.08 (s,1H), 3.69 (s,3H).

Example 7

3-(2,4-Dichloro-5-methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Example 6 was repeated with 37 g (144 mmol) of 3-(2,4-dichloro-5-methylphenyl)-1-methyl-2-pyrazolin-5-one instead of 3-(4-chlorophenyl)-1-methyl-2-pyrazolin-5-one. Yield: 35.1 g;

¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=7.70 (s,1H), 7.46 (s,1H), 6.59 (t,1H), 6.45 (s,1H), 3.84 (s,3H), 2.39 (s,3H).

Example 8

4-Chloro-3-(4-chlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

A solution of 74.0 g (0,549 mol) of sulfuryl chloride in 200 ml of carbon tetrachloride was added slowly to a solution of 128.9 g (0.5 mol) of 3-(4-chlorophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 500 ml of carbon tetrachloride. After the exothermic reaction with evolution of gas had subsided, the reaction mixture was stirred at 20°-25° C.for 2 hours more. The reaction solution was then washed with water, saturated sodium hydrogen carbonate solution and saturated sodium chloridesolution, and finally dried and concentrated. Yield: 139.3 g; ¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=7,79 (d,2H), 7,43 (d,2H), 6,70 (t,1H), 3,85 (s,3H).

Example 9

4-Chloro-3-(2,4-dichloro-5-methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Analogously to Example 8, 35 g (114 mmol) of 3-(2,4-dichloro-5-methylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole were reacted with 16.9 g (125 mmol) of sulfuryl chloride. Yield: 30.8 g; 1H-NMR (270 MHz, in CDCl₃): δ ppm!=7.49 (s,1H), 7.30 (s,1H), 6.74 (t,1H), 3.85 (s,3H), 2.39 (s,3H).

Example 10

3-(3-Dibromomethyl-4-chlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole

10.5 g (58.8 mmol) of N-bromosuccinimide were added to a solution of 3.0 g (9.8 mmol) of 4-chloro-5-difluoromethoxy-3-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole (prepared analogously to Example 8) in 100 ml of carbon tetrachloride. The reaction solution was then heated at reflux for 1 hour while being irradiated with a 150 W high-pressure mercury lamp. Filtration and removalof the solvent under reduced pressure gave 3.9 g of the crude product, which was reacted further without additional purification.

¹ H-NMR (400 MHz, in CDCl₃): δ ppm!=8.56 (s,1H), 7.79 (d,1H), 7.46 (d,1H), 7.15 (d,1H), 6.70 (t,1H), 3.85 (s,3H).

Example 11

3-(5-Dibromomethyl-2,4-dichlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole

Analogously to Example 10, 28 g (82 mmol) of 4-chloro-3-(2,4-dichloro-5-methylphenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole were reacted with 99.3 g (560 mmol) of N-bromosuccinimide. Yield: 49.5 g. ¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=8.08 (s,1H), 7.50 (s,1H), 7.05 (s,1H), 6.75 (t,1H), 3.88 (s,3H).

Example 12

4-Chloro-3-(4-chloro-3-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

At 85° C., 4.65 g (10 mmol) of 3-(3-dibromomethyl-4-chloro-phenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole were introduced a little at a time into 7 ml of concentrated sulfuric acid. The reaction solution was then stirred at 100° C. for 5 minutes, then stirred into 40 ml of ice-water. The solid product formed was filtered off and dried. Yield: 3.0 g;

1H-NMR-(270 MHz, in CDCl₃): δ ppm!=10.50 (s,1H), 8.45 (s,1H), 8.06 (d,1H), 7.52 (d,1H), 6.71 (t,1H), 3.82 (s,3H).

Example 13

4-Chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

Analogously to Example 12, 45.5 g (91 mmol) of 3-(5-dibromomethyl-2,4-dichlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazole were introduced into 65 ml of concentrated sulfuric acid. After working up, 20 g of the product were obtained. ¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=10.41 (s,1H), 8.02 (s,1H), 7.65 (s,1H),6.77 (t,1H), 3.87 (s,3H).

Example 14

Ethyl 3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-2-cyanopropenoate (ib.223)

2.4 g (21 mmol) of ethyl cyanoacetate and 0.3 g (4.2 mmol) of sodium ethanolate were added to a solution of 7.5 g (21 mmol) of 4-chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 70 ml of ethanol. The mixture was stirred for 4 hours then poured into ice-water, after which the solid product was filtered off, washed with n-hexane and then dried. Yield: 4.9 g.

Example 15

Ethyl 3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-2-cyanooxirane-2-carboxylate (Ib.265)

1.4 g (12 mmol) of 30% strength aqueous hydrogen peroxide solution were added to 2.7 g (6 mmol) of ethyl 3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)Phenyl)-2-cyanopropenoate in 30 ml of ethanol. After 12 hours the mixture was poured into water. The product was extracted from the aqueous phase using ethyl acetate, after which the organic phase was dried over magnesium sulfate and then concentrated. Purification of the crude product was carried out by means of column chromatography on silica gel (eluent: hexane/ethyl acetate=4:1). Yield: 1 g.

Example 16

2-Chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoic acid (Ib.001)

85 ml of trifluoroacetic acid were added dropwise to a solution of 34.4 g (70 mmol) of tert-butyl 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-propenoate in 85 ml of dichloromethane. After 3 hours the mixture was concentrated. The residue was triturated with n-hexane, then filtered off and dried. Yield: 19.9 g.

Example 17

2-Chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoyl chloride

3 drops of dimethylformamide and then 11.1 g (87 mmol) of oxalyl chloride were added dropwise to a solution of 12.5 g (29 mmol) of 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoic acid in 300 ml of toluene. The reaction mixture was stirred at reflux temperature for 5 hours and then concentrated. Yield: quantitative.

Example 18

N-Allyl-N-aminocarbonyl-2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenamide (Ib.242)

0.36 g (4.4 mmol) of allylcyanamide were added to a suspension of 2 g (4.4 mmol) of 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)Propenoyl chloride and 0.8 g (5.8 mmol) of potassium carbonate(ground) in 50 ml of tetrahydrofuran. The reaction mixture was stirred at 50 to 60° C. for 5 hours and then concentrated. The residue was taken up in ethyl acetate, after which the organic phase was washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by means of column chromatography on silica gel (eluent: ethyl acetate) followed by crystallization from diisopropyl ether. Yield: 0.2 g.

Example 19

S-(Ethoxycarbonylmethyl) 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)thiopropenoate (ib.068)

0.95 g (7.3 mmol) of pyridine and 0.88 g (7.3 mmol) of ethyl mercaptoacetate were added to a solution of 3.3 g (6.7 mmol) of 2-chloro-3-(2,4-dichloro-5-{4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoyl chloride in 70 ml of tetrahydrofuran. The reaction mixture was stirred for 8 hours and then concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane/ethyl acetate =1:1). Yield: 2.1 g.

Example 20

4-Acetoxytetrahydrofuran-3-yl 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoate (Ib.230)

1.0 g (10.2 mmol) of triethylamine and 0.82 g (5.6 mmol) of 4-acetoxytetrahydrofuran-3-ol were added to a solution of 2.3 g (5.1 mmol}of 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoro-methoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoyl chloride in 50 ml of ethyl acetate. The reaction was stirred for 5 hours and then washed with water, dried over magnesium sulfate and subsequently concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane/ethyl acetate=2:1). Yield: 0.6 g.

Example 21

N-Ethoxy-2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenamide (Ib.064}

0.6 g (3.9 mmol) of carbonyldiimidazole was added to a solution of 1.5 g (3.5 mmol) of 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoic acid in 50 ml of tetrahydrofuran. The reaction mixture was stirred for 1 hour and then 0.6 g (3.9 mmol) of 0-ethylhydroxylamine hemi-dihydrogen sulfate and 0.4 g (3.9 mmol) of triethylamine were added. The reaction mixture was subsequently stirred overnight and then concentrated. The residue was taken up in ethyl acetate, after which the solution obtained was washed with water, dried over magnesium sulfate and finally concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane/40 ethyl acetate=1:1). Yield: 0.6 g.

Example 22

2-(N-Butoxy) iminoethyl 2-chloro-3-(2,4-dichloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propenoate (Ib.075)

0.63 g o(4.6 mmol) of ground potassium carbonate followed dropwise by 0.5 g(3.5 mmol) of 0-butyl-2-chloroacetaldehyde oxime were added to a solution of 1.5 g (3.5 mmol) of 2-chloro-3-(2,4-di-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-phenyl)propenoic acid in 35 ml of dimethylformamide. The mixture was heated at from 50° to 60° C. for 3 hours and then concentrated. The residue was taken up in ethyl acetate, and the resultingorganic phase was then washed with water, dried over magnesium sulfate and finally concentrated. The crude product was purified by chromatography on silica gel (eluent: hexane/ethyl acetate=4:1). Yield: 1.1 g.

Example 23

tert-Butyl 2-chloro-3-(2-chloro-5-(4-chloro-5-difluoro-methoxy-1-methyl-1H-pyrazol-3-yl)phenyl)propanoate (Ia.118) and tert-butyl 3-(2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)phenyl)-2-hydroxypropanoate (Ia.173)

14.1 g (0.10 mol) of copper(II) chloride and 14.7 g (0.14 mol) of tert-butyl nitrite were added to 26.1 g (2.03 mol) of tert-butyl acrylate in 500 ml of acetonitrile. 29.3 g (95 mmol) of 3-(3-amino-4-chlorophenyl)-4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazolewere subsequently added a little at a time to this mixture, and the resulting mixture was then stirred for 3 hours. tert-Butyl methyl ether was then added to the reaction mixture. The resulting organic phase was subsequently washed with 1N hydrochloric acid and aqueous sodium chloride solution, dried over magnesium sulfate and finally concentrated. The crudeproduct was purified by chromatography on silica gel (eluent: hexane/ethyl acetate=4:1). Yield: 21.2 g of α-chloro ester Ia.118 and 3.9 g of α-hydroxy ester Ia.173.

Example 24

4-Chloro-3-(4-cyano-3-nitrophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole

1.1 g (17 mmol) of potassium cyanide were added to a solution of 5.0 g (15.6 mmol) of 4-chloro-3-(4-fluoro-3-nitrophenyl)-5-difluoromethoxy-1-methyl-1H-pyrazolein 70 ml of dimethyl sulfoxide. The solution obtained was then stirred at 50° C. for 5 hours and then at room temperature for 3 days, after which it was poured into ice-water. The product was then extracted from the aqueous phase using methyl tert-butyl ether. The organic phase was finally dried over magnesium sulfate and then concentrated. The crude product was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3:1). Yield: 2.7 g;

¹ H-NMR δ250 MHz, in CDCl₃): δ ppm!=3.88(s,3H); 6.71(t, 1H); 7.95(d,1H); 8.4(m, 1H); 8.93(m,1H).

Example 25

1-Bromomethyl-4-chloro-3-(2,4-dichloro-5-(dibromomethyl)phenyl)-5-difluoromethoxy-1H-pyrazole

A solution of 6 g (12 mmol) of 4-chloro-3-(2,4-dichloro-5-(di-bromomethyl)phenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole and 6.4 g (36 mmol) of N-bromosuccinimide in 800 ml of tetrachloromethane was irradiated for 2 hours with a 150 W high-pressure mercury lamp and a UV lamp. The solids were then removed by filtration, and the filtrate was concentrated. Silica gel chromatography of the residue (eluent: hexane/ethyl acetate=4:1) gave 2 g of the target product. ¹ H-NMR (250 MHz, in CDCl₃): δ ppm!=5.87(s,2H); 6.82(t,1H); 7.03(s,1H); 7.52(s,1H); 8.08(s,1H).

Example 26

4-Chloro-3-(2,4-dichloro-5-(dibromomethyl)phenyl)-5-difluoro-methoxy-1-methoxymethyl-1H-pyrazole

1.3 g (7 mmol) of a 30% strength methanolic sodium methylate solution were added to a solution of 1.2 g (2 mmol) of 1-bromo-methyl-4-chloro-3-(2,4-dichloro-5-(dibromomethyl)phenyl)-5-difluoromethoxy-1H-pyrazole in 30 ml of methanol. The reaction mixture was then heated at reflux temperature for 2.5 hours and then concentrated. The residue was taken up in methyl tert-butyl ether. The ether phase was subsequently washed with water, dried over magnesium sulfate and concentrated. Yield: 0.8 g; ¹ H-NMR (270 MHz, in CDCl₃): δ ppm!=3.45(s,3H); 5.44(s,2H); 6.75(t,1H); 7.05(s,1H); 7.52(s,1H); 8.06(s,1H).

Tables 1-31 below list further compounds I which were prepared in analogy to the Examples or can be prepared either in accordance with the methods described above or by methods which are known per se.

                                      TABLE 1                                      __________________________________________________________________________      ##STR25##                                                                                                         m.p./.sup.1 H-NMR ppm!/                    No. R.sup.1                         MS(mz.sup.-1)                              __________________________________________________________________________     Ia.001                                                                             CHC(Cl)COOH                                                                Ia.002                                                                             CHC(Cl)COOCH.sub.3              98-100° C.                          Ia.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5       59-61° C.                           Ia.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Ia.005                                                                             CHC(Br)COOH                                                                Ia.006                                                                             CHC(Br)COOCH.sub.3              118-121° C.                         Ia.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ia.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ia.009                                                                             CHC(Cl)CONH.sub.2                                                          Ia.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ia.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ia.012                                                                             CHC(Br)CONH.sub.2                                                          Ia.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ia.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Ia.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ia.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Ia.017                                                                             CH(cyclopropylene)                                                         Ia.018                                                                             CH(cyclopentylene)                                                         Ia.019                                                                             CH(cyclohexylene)                                                          Ia.020                                                                              ##STR26##                      140-144° C.                         Ia.021                                                                              ##STR27##                                                                 Ia.022                                                                              ##STR28##                                                                 Ia.023                                                                              ##STR29##                                                                 Ia.024                                                                              ##STR30##                                                                 Ia.025                                                                              ##STR31##                                                                 Ia.026                                                                              ##STR32##                                                                 Ia.027                                                                              ##STR33##                                                                 Ia.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ia.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ia.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ia.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ia.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ia.033                                                                             CHC(CN)COOCH.sub.3                                                         Ia.034                                                                             CH.sub.2CH(CN)COOCH.sub.3                                                  Ia.035                                                                             CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                           Ia.036                                                                             CH.sub.2CH(CN)CONH.sub.2                                                   Ia.037                                                                             CH.sub.2CH(CN)CONHCH.sub.3                                                 Ia.038                                                                             CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                          Ia.039                                                                             CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                         Ia.040                                                                             CH.sub.2CH(Cl)COOCH.sub.3       7.84(s, 1H); 7.77(d, 1H);                                                      7.58(d, 1H); 6.72(t, 1H);                                                      4.68(t, 1H); 3.83(s, 3H);                                                      3.75(s, 3H); 3.59-3,36                                                         (m, 2H)                                    Ia.041                                                                             CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                                               7.84(s, 1H); 7.76(d, 1H);                                                      7.44(d, 1H); 6.70(t, 1H);                                                      4.65(t, 1H); 4.22(q, 2H);                                                      3.80(s, 3H); 3.58-3,37                                                         (m, 2H); 1.25(t, 3H)                       Ia.042                                                                             CH.sub.2CH(Cl)CONH.sub.2                                                   Ia.043                                                                             CH.sub.2CH(Cl)CONHCH.sub.3                                                 Ia.044                                                                             CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                          Ia.045                                                                             CH.sub.2CH(Cl)CONHSO.sub.2CH.sub.3                                         Ia.046                                                                             CH.sub.2CH(Br)COOCH.sub.3       7.82(s, 1H); 7.76(d, 1H);                                                      7.45(d, 1H); 6.69(t, 1H);                                                      4.62(t, 1H); 3.83(s, 3H);                                                      3.74(s, 3H); 3.64(dd, 1H);                                                     3.45(dd, 1H)                               Ia.047                                                                             CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                                               7.82(s, 1H); 7.75(d, 1H),                                                      7.42(d, 1H); 6.67(t, 1H);                                                      4.61(t, 1H); 4.25-4.10                                                         (m, 2H); 3.80(s, 3H);                                                          3.60(dd, 1H); 3.42(dd, 1H);                                                    1.26(t, 3H)                                Ia.048                                                                             CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                        Ia.049                                                                             CH.sub.2CH(Br)CONH.sub.2                                                   Ia.050                                                                             CH.sub.2CH(Br)CONHCH.sub.3                                                 Ia.051                                                                             CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                          Ia.052                                                                             CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                         Ia.053                                                                             CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                         Ia.054                                                                             CHCH-(4-fluorophenyl)                                                      Ia.055                                                                             CHCH-(4-chlorophenyl)           96-98° C.                           Ia.056                                                                             CHCH-(3-trifluoromethylphenyl)  462 M!.sup.+                               Ia.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Ia.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Ia.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Ia.060                                                                             CHC(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ia.061                                                                             CHC(Cl)CONHCH.sub.2COOCH.sub.3                                             Ia.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                    Ia.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Ia.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Ia.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Ia.066                                                                             CHC(Cl)CONHOCH.sub.2CHCHCl                                                 Ia.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ia.068                                                                             CHC(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                       Ia.069                                                                             CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                          Ia.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Ia.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Ia.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Ia.073                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.3                                             Ia.074                                                                             CHC(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ia.075                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                      Ia.076                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ia.077                                                                             CHC(Br)COO-cyclohexyl                                                      Ia.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Ia.079                                                                             CHC(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ia.080                                                                             CHC(Br)CONHCH.sub.2COOCH.sub.3                                             Ia.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                    Ia.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Ia.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Ia.084                                                                             CHC(Br)CONHOCH.sub.2CHCHCl                                                 Ia.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ia.086                                                                             CHC(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                       Ia.087                                                                             CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                          Ia.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Ia.089                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                   Ia.090                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ia.091                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.3                                             Ia.092                                                                             CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ia.093                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                      Ia.094                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ia.095                                                                             CH.sub.2CH(Cl)COO-cyclohexyl    7.80(s, 1H); 7.75(d, 1H);                                                      7.44(d, 1H); 6.71(t, 1H);                                                      4.80(m, 1H); 4.60(t, 1H);                                                      3.81(s, 3H); 4.55-3.36                                                         (m, 2H); 1.84-1.29                                                             (m, 10H)                                   Ia.096                                                                             CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                                                             7.84(s, 1H); 7.77(d, 1H);                                                      7.57(d, 1H); 6.71(t, 1H);                                                      4.58(t, 1H); 3.84(s, 3H);                                                      3.52-3,34(m, 2H);                                                              1.44(s, 9H)                                Ia.097                                                                             CH.sub.2CH(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                                                    7.83(s, 1H); 7.77(d, 1H);                                                      7.45(d, 1H); 6.70(t, 1H);                                                      4.67(t, 1H); 3.94(m, 2H);                                                      3.79(s, 3H); 3.55-3.38                                                         (m, 2H); 1.96(m, 1H);                                                          0.97-0.89(m, 6H)                           Ia.098                                                                             CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                                                          97° C.                              Ia.099                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                 484 M+H!.sup.+, 448 M-Cl!.sup.+            Ia.100                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                                               76-78° C.                           Ia.101                                                                             CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                                                             441 M!.sup.+, 406 M-Cl!.sup.+              Ia.102                                                                             CH.sub.2CH(Cl)CONHOCH.sub.3                                                Ia.103                                                                             CH.sub.2CH(Cl)CONHCCH.sub.2CHCHCl                                                                              487 M!.sup.+, 452 M-Cl!.sup.+              Ia.104                                                                             CH.sub.2CH(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                              Ia.105                                                                             CH.sub.2CH(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                                                    500 M!.sup.+, 465 M-Cl!.sup.+              Ia.106                                                                             CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                   Ia.107                                                                             CH.sub.2CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                                Ia.108                                                                             CH.sub.2C(Cl)(COOC.sub.2 H.sub.5).sub.2                                    Ia.109                                                                             CH.sub.2C(Cl)(COOCH.sub.3).sub.2                                           Ia.110                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.3                                      Ia.111                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                                                   483 M!.sup.+, 448 M-Cl!.sup.+              Ia.112                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5               Ia.113                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ia.114                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ia.115                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                                                    487 M!.sup.+, 452 M-Cl!.sup.+              Ia.116                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ia.117                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                 Ia.118                                                                             CH.sub.2CH(Cl)COOH              7.85(s, 1H); 7.78(d, 1H);                                                      7.60(d, 1H); 7.48(t, 1H);                                                      4.72(t, 1H); 3.80(s, 3H);                                                      3.58-3.30(m, 2H)                           Ia.119                                                                             CH.sub.2CH(Cl)CONH-cyclopropyl  104-105° C.                         Ia.120                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                          497 M!.sup.+, 462 M-Cl!.sup.+              Ia.121                                                                             CH.sub.2CH(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                     525 M!.sup.+, 490 M-Cl!.sup.+              Ia.122                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                                                   8.78(m, 1H); 7.75(m, 1H);                                                      7.58(m, 1H); 7.47(t, 1H):;                                                     4.75(m, 1H); 4.37-4.16                                                         (m, 1H); 3.80(s, 3H);                                                          3.61-3.48(m, 2H);                                                              3.35-3.20(m, 2H),                                                              1.60-1.05(m, 3H);                                                              0.90-0.52(m, 6H)                           Ia.123                                                                             CH.sub.2CH(Cl)CO-(2methoxycarbonyl-pyrrolidin-1-yl)                                                            509 M!.sup.+, 474 M-Cl!.sup.+              Ia.124                                                                             CH.sub.2CH(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                             Ia.125                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ia.126                                                                             CH.sub.2CH(Cl)CON(CN)-cyclopropyl                                          Ia.127                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2CHCH.sub.2                                    Ia.128                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ia.129                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)-cyclopropyl                                  Ia.130                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ia.131                                                                             CH.sub.2CH(Cl)COO-(4-acetoxytetra-hydrofuran-3-yl)                         Ia.132                                                                             CH.sub.2CH(Br)COO-cyclohexyl    7.84(s, 1H); 7.76(d, 1H);                                                      7.45(d, 1H); 6.72(t, 1H);                                                      4.80(m, 1H); 4.61(t, 1H)                                                       3.85(s, 3H); 3.63-3.48                                                         (m, 2H); 1.88-1.28                                                             (m, 10H)                                   Ia.133                                                                             CH.sub.2 CH(Br)COOC(CH.sub.3).sub.3                                                                            7.83(s, 1H); 7.76(d, 1H);                                                      7.44(d, 1H); 6.70(t, 1H);                                                      4.53(t, 1H); 3.84(s, 3H);                                                      3.58-3.42(m, 2H);                                                              1.43(s, 9H)                                Ia.134                                                                             CH.sub.2CH(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                                                    7.82(s, 1H); 7.75(d, 1H);                                                      7.44(d, 1H); 6.70(t, 1H);                                                      4.66(t, 1H); 3.92(m, 2H)                                                       3.80(s, 3H); 3.62-3.45                                                         (m, 2H); 1.96(m, 1H)                                                           0.93(m, 6H)                                Ia.135                                                                             CH.sub.2CH(Br)CONHCH.sub.2COOCH.sub.3                                                                          102-103° C.                         Ia.136                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                             Ia.137                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                                               541 M!.sup.+, 506 M-Cl!.sup.+              Ia.138                                                                             CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                         Ia.139                                                                             CH.sub.2CH(Br)CONHOCH.sub.3                                                Ia.140                                                                             CH.sub.2CH(Br)CONHOCH.sub.2CHCHCl                                          Ia.141                                                                             CH.sub.2CH(Br)CONHOCH.sub.2 -(4-chlorophenyl)                              Ia.142                                                                             CHCH(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                      Ia.143                                                                             CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                   Ia.144                                                                             CH.sub.2CH(Br)COSCH.sub.2 -(4-chlorophenyl)                                Ia.145                                                                             CH.sub.2C(Br)(COOC.sub.2 H.sub.5).sub.2                                    Ia.146                                                                             CH.sub.2C(Br)(COOCH.sub.3).sub.2                                           Ia.147                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.3                                      Ia.148                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Ia.149                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ia.150                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ia.151                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ia.152                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                Ia.153                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ia.154                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                 Ia.155                                                                             CH.sub.2CH(Br)COOH              7.91(s, 1H), 7.70(d, 1H);                                                      7.47(d, 1H); 6.72(t, 1H);                                                      4.66(t, 1H); 3.86(s, 3H);                                                      3.68-3.43(m, 2H)                           Ia.156                                                                             CH.sub.2CH(Br)CONH-cyclopropyl  121-122° C.                         Ia.157                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                          541 M!.sup.+, 462 M-Br!.sup.+              Ia.158                                                                             CH.sub.2CH(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                     569 M!.sup.+, 490 M-Br!.sup.+              Ia.159                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                                                   569 M!.sup.+, 534 M-Cl!.sup.+              Ia.160                                                                             CH.sub.2CH(Br)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                                                           553 M!.sup.+, 474 M-Br!.sup.+              Ia.161                                                                             CH.sub.2CH(Br)CONH-(tetrahydro-furan-2-on-3-yl)                            Ia.162                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ia.163                                                                             CH.sub.2CH(Br)CON(CN)-cyclopropyl                                          Ia.164                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2CHCH.sub.2                                    Ia.165                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ia.166                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)-cyclopropyl                                  Ia.167                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ia.168                                                                             CH.sub.2CH(Br)COO-(4-acetoxytetra-hydrofuran-3-yl)                         Ia.169                                                                             CH.sub.2CH(OH)COOH                                                         Ia.170                                                                             CH.sub.2CH(OH)COOCH.sub.3                                                  Ia.171                                                                             CH.sub.2CH(OH)COOC.sub.2 H.sub.5                                           Ia.172                                                                             CH.sub.2CH(OH)COOCH.sub.2CHNOCH.sub.3                                      Ia.173                                                                             CH.sub.2CH(OH)COOC(CH.sub.3).sub.3                                                                             436 M!.sup.+                               Ia.174                                                                             CH.sub.2CH(OH)CONH.sub.2                                                   Ia.175                                                                             CH.sub.2CH(OH)CONHCH.sub.3                                                 Ia.176                                                                             CH.sub.2CH(OH)CONH-cyclopropyl                                             Ia.177                                                                             CH.sub.2CH(OCH.sub.3)COOH       394 M!.sup.+                               Ia.178                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.3                                           Ia.179                                                                             CH.sub.2CH(OCH.sub.3)COOC.sub.2 H.sub.5                                    Ia.180                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.2CHNOCH.sub.3                               Ia.181                                                                             CH.sub.2CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                                                      450 M!.sup.+                               Ia.182                                                                             CH.sub.2CH(OCH.sub.3)CONH.sub.2                                            Ia.183                                                                             CH.sub.2CH(OCH.sub.3)CONHCH.sub.3                                          Ia.184                                                                             CH.sub.2CH(OCH.sub.3)CONH-cyclopropyl                                      Ia.185                                                                             CH.sub.2CH(OCOCH.sub.3)COOH                                                Ia.186                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.3                                         Ia.187                                                                             CH.sub.2CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                  Ia.188                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.2CHNOCH.sub.3                             Ia.189                                                                             CH.sub.2CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                                Ia.190                                                                             CH.sub.2CH(OCOCH.sub.3)CONH.sub.2                                          Ia.191                                                                             CH.sub.2CH(OCOCH.sub.3)CONHCH.sub.3                                        Ia.192                                                                             CH.sub.2CH(OCOCH.sub.3)CONH-cyclopropyl                                    Ia.193                                                                             CH.sub.2CH(NH.sub.2)COOH                                                   Ia.194                                                                             CH.sub.2CH(NH.sub.2)COOCH.sub.3                                            Ia.195                                                                             CH.sub.2CH(NH.sub.2)COOC.sub.2 H.sub.5                                     Ia.196                                                                             CH.sub.2CH(NH.sub.2)COOC(CH.sub.3).sub.3                                   Ia.197                                                                             CH.sub.2CH(NH.sub.2)CONH.sub.2                                             Ia.198                                                                             CH.sub.2CH(NH.sub.2)CONHCH.sub.3                                           Ia.199                                                                             CH.sub.2CH(N.sub.3)COOH                                                    Ia.200                                                                             CH.sub.2CH(N.sub.3)COOCH.sub.3                                             Ia.201                                                                             CH.sub.2CH(N.sub.3)COOC.sub.2 H.sub.5                                      Ia.202                                                                             CH.sub.2CH(N.sub.3)COOC(CH.sub.3).sub.3                                    Ia.203                                                                             CH.sub.2CH(N.sub.3)CONH.sub.2                                              Ia.204                                                                             CH.sub.2CH(N.sub.3)CONHCH.sub.3                                            Ia.205                                                                             CH.sub.2CH(NHCOCH.sub.3)COOH                                               Ia.206                                                                             CH.sub.2CH(NHCOCH.sub.3)COOCH.sub.3                                        Ia.207                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                 Ia.208                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                               Ia.209                                                                             CH.sub.2CH(NHCOCH.sub.3)CONH.sub.2                                         Ia.210                                                                             CH.sub.2CH(NHCOCH.sub.3)CONHCH.sub.3                                       Ia.211                                                                             CH.sub.2CH.sub.2 -cyclohexyl                                               Ia.212                                                                             CH.sub.2CH.sub.2 -cyclopentyl                                              Ia.213                                                                             CH.sub.2CH.sub.2 -cyclopropyl                                              Ia.214                                                                             CH.sub.2CH.sub.2 -phenyl                                                   Ia.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Ia.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Ia.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Ia.218                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                   Ia.219                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ia.220                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -4-chlorophenyl)                            Ia.221                                                                             CHC(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                        Ia.222                                                                             CHC(Cl)COO(4-acetoxytetrahydrofuran-3-yl)                                  Ia.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Ia.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                             Ia.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ia.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ia.227                                                                             CHC(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                              Ia.228                                                                             CHC(Cl)CONH(tetrahydrofuran-2-on-3-yl)                                     Ia.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                             Ia.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Ia.231                                                                             CHC(Cl)CON(CN)CH.sub.2CHCH.sub.2                                           Ia.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ia.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Ia.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                   Ia.235                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                           Ia.236                                                                             CHC(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                        Ia.237                                                                             CHC(Br)COO(4-acetoxytetrahydrofuran-3-yl)                                  Ia.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Ia.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                             Ia.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ia.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ia.242                                                                             CHC(Br) CO(2-methoxycarbonyl-pyrrolidin-1-yl)                              Ia.243                                                                             CHC(Br)CONH-(tetrahydrofuran-2-on-3-yl)                                    Ia.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                             Ia.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Ia.246                                                                             CHC(Br)CON(CN)CH.sub.2CHCH.sub.2                                           Ia.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ia.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Ia.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                   Ia.250                                                                             CH.sub.2CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                   Ia.251                                                                             CH.sub.2CH(Br)CON(C.sub.2 H.sub.5).sub.2                                   Ia.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ia.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ia.254                                                                              ##STR34##                                                                 Ia.255                                                                              ##STR35##                                                                 Ia.256                                                                              ##STR36##                                                                 Ia.257                                                                              ##STR37##                                                                 Ia.258                                                                              ##STR38##                                                                 Ia.259                                                                              ##STR39##                                                                 Ia.260                                                                              ##STR40##                                                                 Ia.261                                                                              ##STR41##                                                                 Ia.262                                                                              ##STR42##                                                                 __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR43##                                                                                                      m.p./.sup.1 H-NMR ppm!/                       No. R.sup.1                      MS mz.sup.-1 !                                __________________________________________________________________________     Ib.001                                                                             CHC(Cl)COOH                  182-185° C.                            Ib.002                                                                             CHC(Cl)COOCH.sub.3           8.10(s, 1H); 8.07(s, 1H);                                                      7.62(s, 1H); 6.74(t, 1H);                                                      3.95/s, 3H); 3.85(s, 3H)                      Ib.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5    110-112° C.                            Ib.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Ib.005                                                                             CHC(Br)COOH                                                                Ib.006                                                                             CHC(Br)COOCH.sub.3           8.30(s, 1H); 8.00(s, 1H);                                                      7.60(s, 1H); 6.72(t, 1H);                                                      3.94(s, 3H); 3.86(s, 3H)                      Ib.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ib.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ib.009                                                                             CHC(Cl)CONH.sub.2                                                          Ib.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ib.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ib.012                                                                             CHC(Br)CONH.sub.2                                                          Ib.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ib.014                                                                             CHC(Br)CON(CH.sub.3)                                                       Ib.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ib.016                                                                             CHC(Cl)CONH-cyclopropyl      78-81° C.                              Ib.017                                                                             CH(cyclopropylene)                                                         Ib.018                                                                             CH(cyclopentylene)                                                         Ib.019                                                                             CH(cyclohexylene)                                                          Ib.020                                                                              ##STR44##                   169-171° C.                            Ib.021                                                                              ##STR45##                                                                 Ib.022                                                                              ##STR46##                                                                 Ib.023                                                                              ##STR47##                                                                 Ib.024                                                                              ##STR48##                                                                 Ib.025                                                                              ##STR49##                                                                 Ib.026                                                                              ##STR50##                                                                 Ib.027                                                                              ##STR51##                                                                 Ib.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ib.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ib.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ib.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ib.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ib.033                                                                             CHC(CN)COOCH.sub.3                                                         Ib.034                                                                             CH.sub.2CH(CN)COOCH.sub.3                                                  Ib.035                                                                             CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                           Ib.036                                                                             CH.sub.2CH(CN)CONH.sub.2                                                   Ib.037                                                                             CH.sub.2CH(CN)CONHCH.sub.3                                                 Ib.038                                                                             CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                          Ib.039                                                                             CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                         Ib.040                                                                             CH.sub.2CH(Cl)COOCH.sub.3    7.52(s, 1H); 7.36(s, 1H);                                                      6.71(t, 1H); 4.60(t, 1H);                                                      3.84(s, 3H); 3.75(s, 3H);                                                      3.50(dd, 1H); 3.28(dd, 1H)                    Ib.041                                                                             CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                                            7.54(s, 1H); 7.36(s, 1H);                                                      6.73(t, 1H); 4.59(t, 1H);                                                      4.25-4,15(m, 2H);                                                              3.85(s, 3H); 3.50(dd, 1H);                                                     3.30(dd, 1H); 1.25(s, 3H)                     Ib.042                                                                             CH.sub.2CH(Cl)CONH.sub.2                                                   Ib.043                                                                             CH.sub.2CH(Cl)CONHCH.sub.3                                                 Ib.044                                                                             CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                          Ib.045                                                                             CH.sub.2CH(Cl)CONHSO.sub.2CH.sub.3                                         Ib.046                                                                             CH.sub.2CH(Br)COOCH.sub.3    7.52(s, 1H); 7.34(s, 1H);                                                      6.71(t, 1H); 4.55(t, 1H);                                                      3.82(s, 3H); 3.74(s, 3H);                                                      3.55(dd, 1H); 3.36(dd, 1H)                    Ib.047                                                                             CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                                            7.52(s, 1H); 7.36(s, 1H);                                                      6.70(t, 1H); 4.53(t, 1H);                                                      4.28-4,10(m, 2H);                                                              3.84(s, 3H); 3.56(dd, 1H);                                                     3.39(dd, 1H); 1.25(t, 3H)                     Ib.048                                                                             CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                        Ib.049                                                                             CH.sub.2CH(Br)CONH.sub.2                                                   Ib.050                                                                             CH.sub.2CH(Br)CONHCH.sub.3                                                 Ib.051                                                                             CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                          Ib.052                                                                             CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                         Ib.053                                                                             CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                         Ib.054                                                                             CHCH-(4-fluorophenyl)        446 M!.sup.+                                  Ib.055                                                                             CHCH-(4-chlorophenyl)        462 M!.sup.+                                  Ib.056                                                                             CHCH-(4-trifluoromethylphenyl)                                             Ib.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Ib.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Ib.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3  8.08(s, 1H); 8.01(s, 1H);                                                      7.60(s, 1H); 6.73(t, 1H);                                                      3.86(s, 3H); 1.60(s, 9H)                      Ib.060                                                                             CHC(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ib.061                                                                             CHC(Cl)CONHCH.sub.2COOCH.sub.3                                             Ib.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                     7.90(m, 1H); 7.59(s, 1H);                                                      7.15-7,04(m, 1H);                                                              6.72(t, 1H); 4.22(s, 2H);                                                      3.85(s, 3H); 3.80(s, 3H);                                                      3.25-3,05(m, 3H)                              Ib.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Ib.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5  9.19(s, 1H); 8.15(s, 1H);                                                      7.88(s, 1H); 7.61(s, 1H);                                                      6.72(t, 1H); 4.08(q, 2H);                                                      3.85(s, 3H); 1.33(t, 3H)                      Ib.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Ib.066                                                                             CHC(Cl)CONHOCH.sub.2CHCHCl   519 M!.sup.+, 484 M-Cl!.sup.+                 Ib.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                                                      569 M!.sup.+                                  Ib.068                                                                             CHC(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                                                        532 M!.sup.+, 497 M-Cl!.sup.+                 Ib.069                                                                             CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                                                           8.06(s, 1H); 8.03(s, 1H);                                                      7.61(s, 1H); 6.72(t, 1H);                                                      3.86(s, 3H); 3,00(t, 2H);                                                      1,70(m, 2H); 1,03(t, 3H);                     Ib.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Ib.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Ib.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Ib.073                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.3                                             Ib.074                                                                             CHC(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ib.075                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                                                       8.12(m, 1H); 8.08(m, 1H);                                                      7.62(s, 1H); 7.53 and 6.88                                                     (2t, together 1H);                                                             6.72(t, 1H); 5.10 and 4.89                                                     (2d, together 2H);                                                             4.10(m, 2H); 3.85(s, 3H);                                                      1.63(q, 2H); 1.40(q, 2H),                                                      0.95( t, 3H)                                  Ib.076                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ib.077                                                                             CHC(Br)COO-cyclohexyl                                                      Ib.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Ib.079                                                                             CHC(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ib.080                                                                             CHC(Br)CONHCH.sub.2COOCH.sub.3                                             Ib.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                    Ib.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Ib.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Ib.084                                                                             CHC(Br)CONHOCH.sub.2CHCHCl                                                 Ib.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ib.086                                                                             CHC(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                       Ib.087                                                                             CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                          Ib.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Ib.089                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                   Ib.090                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ib.091                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.3                                             Ib.092                                                                             CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ib.093                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                      Ib.094                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ib.095                                                                             CH.sub.2CH(Cl)COO-cyclohexyl 7.52(s, 1H); 7.35(s, 1H);                                                      6.70(t, 1H); 4.79(m, 1H)                                                       4.56(t, 1H); 3.83(s, 3H);                                                      3.50(dd, 1H); 3.29(dd, 1H);                                                    1.90-1.15(m, 10H)                             Ib.096                                                                             CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                                                          7.53(s, 1H); 7.36(s, 1H);                                                      6.71(t, 1H); 4.49(t, 1H);                                                      3.83(s, 3H); 3.45(dd, 1H);                                                     3.24(dd, 1H); 1.44(s, 9H)                     Ib.097                                                                             CH.sub.2CH(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                                                 7.54(s, 1H); 7.35(s, 1H);                                                      6.70(t, 1H); 4.60(t, 1H)                                                       3.90(m, 2H); 3.83(s, 3H);                                                      3.50(dd, 1H); 3.28(dd, 1H);                                                    1.91(m, 1H); 0.89(d, 6H).                     Ib.098                                                                             CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                                                       503 M!.sup.+, 468 M-Cl!.sup.+                 Ib.099                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                              518 M+H!.sup.+,                                                                482 M-Cl!.sup.+                               Ib.100                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                           Ib.101                                                                             CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                         Ib.102                                                                             CH.sub.2CH(Cl)CONHOCH.sub.3                                                Ib.103                                                                             CH.sub.2CH(Cl)CONHOCH.sub.2CHCHCl                                          Ib.104                                                                             CH.sub.2CH(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                              Ib.105                                                                             CH.sub.2CH(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                Ib.106                                                                             CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                   Ib.107                                                                             CH.sub.2CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                                Ib.108                                                                             CH.sub.2C(Cl)(COOC.sub.2 H.sub.5).sub.2                                    Ib.109                                                                             CH.sub.2C(Cl)(COOCH.sub.3).sub.2                                           Ib.110                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.3                                      Ib.111                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Ib.112                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5               Ib.113                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ib.114                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ib.115                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                Ib.116                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ib.117                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-                                  chlorophenyl)                                                              Ib.118                                                                             CH.sub.2CH(Cl)COOH           125-127° C.                            Ib.119                                                                             CH.sub.2CH(Cl)CONH-cyclopropyl                                                                              7.64(s, 1H); 7.38(s, 1H);                                                      6.71(t, 1H); 6.55(s, 1H);                                                      4.56(dd, 1H); 3.84 (s, 3H);                                                    3.73(dd, 1H); 3.20(dd, 1H);                                                    2.72(m, 1H); 0.80(m, 2H);                                                      0.64(m, 2H)                                   Ib.120                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                       7.80(m, 1H); 7,59 and                                                          7.53(2s, together                                                              1H); 7.40(t, 1H);                                                              5.27-5.07(m, 1H);                                                              4.48-4.00(m, 4H);                                                              3.82(s, 3H); 3.35(m, 2H);                                                      3.14 and 2.88 (2s,                                                             together                                                                       3H); 1.20(t, 3H)                              Ib.121                                                                             CH.sub.2CH(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                  7.52(s, 1H); 7.39(s, 1H);                                                      6.92(d, 1H); 6.71(t, 1H);                                                      4.65(dd, 1H); 4.52(dd, 1H);                                                    4.25-4.10(m, 2H);                                                              3.83(s, 3H); 3.75(m, 1H);                                                      3.17(m, 1H); 2.20(m, 1H);                                                      1.28(t, 3H); 0.90(m, 6H)                      Ib.122                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                                                560 M+H!.sup.+,                                                                524 M-Cl!.sup.+                               Ib.123                                                                             CH.sub.2CH(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                                                        544 M+H!.sup.+,                                                                508 M-Cl!.sup.+                               Ib.124                                                                             CH.sub.2CH(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                             Ib.125                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ib.126                                                                             CH.sub.2CH(Cl)CON(CN)-cyclopropyl                                                                           7.55(s, 1H); 7.38(s, 1H);                                                      6.71(t, 1H); 5.05(m, 1H);                                                      3.84(s, 3H); 3.52(dd, 1H);                                                     3.38(dd, 1H); 3.07(m, 1H);                                                     1.12-0.80 (m, 4H)                             Ib.127                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2CHCH.sub.2                                    Ib.128                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ib.129                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)-cyclopropyl                                  Ib.130                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ib.131                                                                             CH.sub.2CH(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                          Ib.132                                                                             CH.sub.2CH(Br)COO-cyclohexyl 7.52(s, 1H); 7.34(s, 1H);                                                      6.70(t, 1H); 4.78(m, 1H);                                                      4.53(t, 1H); 3.84(s, 3H);                                                      3.55(dd, 1H); 3.38(dd, 1H);                                                    1.90-1.20(m, 10H)                             Ib.133                                                                             CH.sub.2CH(Br)COOC(CH.sub.3).sub.3                                                                          7.52(s, 1H); 7.35(s, 1H);                                                      6.70(t, 1H); 4.45(t, 1H);                                                      3.83(s, 3H); 3.50(dd, 1H);                                                     3.32(dd, 1H); 1.41(s, 9H).                    Ib.134                                                                             CH.sub.2CH(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                                                 7.53(s, 1H); 7.35(s, 1H);                                                      6.70(t, 1H); 4.57(t, 1H);                                                      3.92(m, 2H); 3.82(s, 3H);                                                      3.56(dd, 1H); 3.37(dd, 1H);                                                    1.93(m, 1H); 0.90(d, 6H);                     Ib.135                                                                             CH.sub.2CH(Br)CONHCH.sub.2COOCH.sub.3                                      Ib.136                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                             Ib.137                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                           Ib.138                                                                             CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                         Ib.139                                                                             CH.sub.2CH(Br)CONHOCH.sub.3                                                Ib.140                                                                             CH.sub.2CH(Br)CONHOCH.sub.2CHCHCl                                          Ib.141                                                                             CH.sub.2CH(Br)CONHOCH.sub.2 -(4-chlorophenyl)                              Ib.142                                                                             CH.sub.2CH(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                Ib.143                                                                             CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                   Ib.144                                                                             CH.sub.2CH(Br)COSCH.sub.2 -(4-chlorophenyl)                                Ib.145                                                                             CH.sub.2C(Br)(COOC.sub.2 H.sub.5).sub.2                                    Ib.146                                                                             CH.sub.2C(Br)(COOCH.sub.3).sub.2                                           Ib.147                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.3                                      Ib.148                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Ib.149                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5               Ib.150                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ib.151                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ib.152                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                Ib.153                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ib.154                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-                                  chlorophenyl)                                                              Ib.155                                                                             CH.sub.2CH(Br)COOH           7.81(s, 1H); 7.51(s, 1H);                                                      7.39(t, 1H); 4.69(t, 1H);                                                      3.80(s, 3H); 3.53(dd, 1H);                                                     3.34(dd, 1H)                                  Ib.156                                                                             CH.sub.2CH(Br)CONH-cyclopropyl                                             Ib.157                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                      Ib.158                                                                             CH.sub.2CH(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                  7.51(s, 1H); 7.39(s, 1H);                                                      6.70(t, 1H); 6.68(d, 1H);                                                      4.63(m, 1H); 4.50(m, 1H);                                                      4.25-4.13(m, 2H);                                                              3.83(s, 3H); 3.71(dd, 1H)                                                      3.33(dd, 1H);                                                                  2.25-2.08(m, 1H);                                                              1.28(m, 3H);                                                                   0.98-0.80(m, 6H)                              Ib.159                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3               Ib.160                                                                             CH.sub.2CH(Br)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                       Ib.161                                                                             CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                             Ib.162                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ib.163                                                                             CH.sub.2CH(Br)CON(CN)-cyclopropyl                                          Ib.164                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2CHCH.sub.2                                    Ib.165                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ib.166                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)-cyclopropyl                                  Ib.167                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ib.168                                                                             CH.sub.2CH(Br)COO(4-acetoxytetrahydrofuran-3-yl)                           Ib.169                                                                             CH.sub.2CH(OH)COOH                                                         Ib.170                                                                             CH.sub.2CH(OH)COOCH.sub.3                                                  Ib.171                                                                             CH.sub.2CH(OH)COOC.sub.2 H.sub.5                                           Ib.172                                                                             CH.sub.2CH(OH)COOCH.sub.2CHNOCH.sub.3                                      Ib.173                                                                             CH.sub.2CH(OH)COOC(CH.sub.3).sub.3                                         Ib.174                                                                             CH.sub.2CH(OH)CONH.sub.2                                                   Ib.175                                                                             CH.sub.2CH(OH)CONHCH.sub.3                                                 Ib.176                                                                             CH.sub.2CH(OH)CONH-cyclopropyl                                             Ib.177                                                                             CH.sub.2CH(OCH.sub.3)COOH                                                  Ib.178                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.3                                           Ib.179                                                                             CH.sub.2CH(OCH.sub.3)COOC.sub.2 H.sub.5                                    Ib.180                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.2CHNOCH.sub.3                               Ib.181                                                                             CH.sub.2CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                  Ib.182                                                                             CH.sub.2CH(OCH.sub.3)CONH.sub.2                                            Ib.183                                                                             CH.sub.2CH(OCH.sub.3)CONHCH.sub.3                                          Ib.184                                                                             CH.sub.2CH(OCH.sub.3)CONH-cyclopropyl                                      Ib.185                                                                             CH.sub.2CH(OCOCH.sub.3)COOH                                                Ib.186                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.3                                         Ib.187                                                                             CH.sub.2CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                  Ib.188                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.2CHNOCH.sub.3                             Ib.189                                                                             CH.sub.2CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                                Ib.190                                                                             CH.sub.2CH(OCOCH.sub.3)CONH.sub.2                                          Ib.191                                                                             CH.sub.2CH(OCOCH.sub.3)CONHCH.sub.3                                        Ib.192                                                                             CH.sub.2CH(OCOCH.sub.3)CONH-cyclopropyl                                    Ib.193                                                                             CH.sub.2CH(NH.sub.2)COOH                                                   Ib.194                                                                             CH.sub.2CH(NH.sub.2)COOCH.sub.3                                            Ib.195                                                                             CH.sub.2CH(NH.sub.2)COOC.sub.2 H.sub.5                                     Ib.196                                                                             CH.sub.2CH(NH.sub.2)COOC(CH.sub.3).sub.3                                   Ib.197                                                                             CH.sub.2CH(NH.sub.2)CONH.sub.2                                             Ib.198                                                                             CH.sub.2CH(NH.sub.2)CONHCH.sub.3                                           Ib.199                                                                             CH.sub.2CH(N.sub.3)COOH                                                    Ib.200                                                                             CH.sub.2CH(N.sub.3)COOCH.sub.3                                             Ib.201                                                                             CH.sub.2CH(N.sub.3)COOC.sub.2 H.sub.5                                      Ib.202                                                                             CH.sub.2CH(N.sub.3)COOC(CH.sub.3).sub.3                                    Ib.203                                                                             CH.sub.2CH(N.sub.3)CONH.sub.2                                              Ib.204                                                                             CH.sub.2CH(N.sub.3)CONHCH.sub.3                                            Ib.205                                                                             CH.sub.2CH(NHCOCH.sub.3)COOH                                               Ib.206                                                                             CH.sub.2CH(NHCOCH.sub.3)COOCH.sub.3                                        Ib.207                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                 Ib.208                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                               Ib.209                                                                             CH.sub.2CH(NHCOCH.sub.3)CONH.sub.2                                         Ib.210                                                                             CH.sub.2CH(NHCOCH.sub.3)CONHCH.sub.3                                       Ib.211                                                                             CH.sub.2CH.sub.2 -cyclohexyl                                               Ib.212                                                                             CH.sub.2CH.sub.2 -cyclopentyl                                              Ib.213                                                                             CH.sub.2CH.sub.2 -cyclopropyl                                              Ib.214                                                                             CH.sub.2CH.sub.2 -phenyl                                                   Ib.215                                                                             CHC(CN)COOC.sub.2 H.sub.5    135-137° C.                            Ib.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Ib.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Ib.218                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                                                    8.17-8.08(m, 2H);                                                              7.61(s, 1H); 7.60 and 6.90                                                     (2t, together 1H);                                                             6.72(t, 1H); 6.00(m, 1H);                                                      5.39-5.23(m, 2H);                                                              5.11 and 4.89(2d,                                                              together 2H); 4.63                                                             (m, 2H); 3.85(s, 3H)                          Ib.219                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ib.220                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                                                            611 M!.sup.+                                  Ib.221                                                                             CHC(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-                                         chlorophenyl)                                                              Ib.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                                                                  8.07(s, 1H); 8.03(s, 1H);                                                      7.94(s, 1H); 7.41(t, 1H);                                                      5.51(q, 1H); 5.40(q, 1H);                                                      4.10-3.75(m, 4H);                                                              3.83(s, 3H); 2.03(s, 3H)                      Ib.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Ib.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                              7.96-7.86(m, 1H);                                                              7.60(s, 1H);                                                                   7.15-7.04(m, 1H);                                                              6.72(t, 1H);                                                                   4.30-4.15(m, 4H);                                                              3.85(s, 3H);                                                                   3.27-3.05(m, 3H);                                                              1.35-1.25(m, 3H)                              Ib.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                         8.15(s, 1H); 7.92(s, 1H);                                                      7.62(s, 1H); 7.26(d, 1H);                                                      6.73(t, 1H); 4.62(dd, 1H);                                                     4.26(q, 2H); 3.85(s, 3H);                                                      2.28(m, 1H); 1.32(t, 3H);                                                      0.98(m, 6H)                                   Ib.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ib.227                                                                             CHC(Cl)CO(2-methoxycarbonyl-pyrrolidin-1-yl)                               Ib.228                                                                             CHC(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                                    Ib.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                                                              8.02(s, 1H); 7.63(m, 2H);                                                      6.74(t, 1H); 3.86(s, 3H);                                                      3.74(t, 2H); 1.80(m, 2H);                                                      1.45(q, 2H); 1.00(t, 3H)                      Ib.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Ib.231                                                                             CHC(Cl)CON(CN)CH.sub.2CHCH.sub.2                                           Ib.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ib.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                                                          127-129° C.                            Ib.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                                                    110-112° C.                            Ib.235                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                           Ib.236                                                                             CHC(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-                                         chlorophenyl)                                                              Ib.237                                                                             CHC(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                                 Ib.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Ib.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                             Ib.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ib.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ib.242                                                                             CHC(Br)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                              Ib.243                                                                             CHC(Br)CONH-(tetrahydrofuran-2-on-3-yl)                                    Ib.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                             Ib.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Ib.246                                                                             CHC(Br)CON(CN)CH.sub.2CHCH.sub.2                                           Ib.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ib.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Ib.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                   Ib.250                                                                             CH.sub.2CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                   Ib.251                                                                             CH.sub.2CH(Br)CON(C.sub.2 H.sub.5).sub.2                                   Ib.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ib.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                                                           485 M!.sup.+, 450 M-Cl!.sup.+                 Ib.254                                                                              ##STR52##                                                                 Ib.255                                                                              ##STR53##                                                                 Ib.256                                                                              ##STR54##                                                                 Ib.257                                                                              ##STR55##                   7.63(s, 1H); 7.48(s, 1H); 6.71(t, 1H);                                         4.73(s, 1H); 4.45(q, 2H); 3.85(s, 3H);                                         1.42(t, 3H)                                   Ib.258                                                                              ##STR56##                                                                 Ib.259                                                                              ##STR57##                                                                 Ib.260                                                                              ##STR58##                                                                 Ib.261                                                                              ##STR59##                                                                 Ib.262                                                                              ##STR60##                                                                 __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR61##                                                                                                         m.p./.sup.1 H-NMR ppm!                     No. R.sup.1                         MS mz.sup.-1 !                             __________________________________________________________________________     Ic.001                                                                             CHC(Cl)COOH                                                                Ic.002                                                                             CHC(Cl)COOCH.sub.3              91° C.                              Ic.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5       88-89° C.                           Ic.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2    8.25(d, 1H); 8.10(s, 1H);                                                      7.34(d, 1H); 6.73(t, 1H);                                                      5.20(m, 1H); 3.85(s, 3H);                                                      1.38(d, 6H);                               Ic.005                                                                             CHC(Br)COOH                                                                Ic.006                                                                             CHC(Br)COOCH.sub.3              99° C.                              Ic.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ic.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ic.009                                                                             CHC(Cl)CONH.sub.2                                                          Ic.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ic.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ic.012                                                                             CHC(Br)CONH.sub.2                                                          Ic.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ic.014                                                                             CHC(Br)CON(CH.sub.3)                                                       Ic.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ic.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Ic.017                                                                             CH(cyclopropylene)                                                         Ic.018                                                                             CH(cyclopentylene)                                                         Ic.019                                                                             CH(cyclohexylene)                                                          Ic.020                                                                              ##STR62##                      123-125° C.                         Ic.021                                                                              ##STR63##                                                                 Ic.022                                                                              ##STR64##                                                                 Ic.023                                                                              ##STR65##                                                                 Ic.024                                                                              ##STR66##                                                                 Ic.025                                                                              ##STR67##                                                                 Ic.026                                                                              ##STR68##                                                                 Ic.027                                                                              ##STR69##                                                                 Ic.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ic.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ic.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ic.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ic.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ic.033                                                                             CHC(CN)COOCH.sub.3                                                         Ic.034                                                                             CH.sub.2CH(CN)COOCH.sub.3                                                  Ic.035                                                                             CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                           Ic.036                                                                             CH.sub.2CH(CN)CONH.sub.2                                                   Ic.037                                                                             CH.sub.2CH(CN)CONHCH.sub.3                                                 Ic.038                                                                             CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                          Ic.039                                                                             CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                         Ic.040                                                                             CH.sub.2CH(Cl)COOCH.sub.3       7.50(d, 1H); 7.25(d, 1H);                                                      6.70(t, 1H); 4.61(dd, 1H);                                                     3.85(s, 3H); 3.78(s, 3H);                                                      3.54(dd, 1H); 3.30(dd, 1H)                 Ic.041                                                                             CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                                               7.50(d, 1H); 7.26(d, 1H);                                                      6.70(t, 1H); 4.57(t, 1H);                                                      4.22(q, 2H); 3.84(s, 3H);                                                      3.51(dd, 1H); 3.28(dd, 1H);                                                    1.25(t, 3H)                                Ic.042                                                                             CH.sub.2CH(Cl)CONH.sub.2                                                   Ic.043                                                                             CH.sub.2CH(Cl)CONHCH.sub.3                                                 Ic.044                                                                             CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                          Ic.045                                                                             CH.sub.2CH(Cl)CONHSO.sub.2CH.sub.3                                         Ic.046                                                                             CH.sub.2CH(Br)COOCH.sub.3                                                  Ic.047                                                                             CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                                               7.50(d, 1H); 7.25(d, 1H);                                                      6.70(t, 1H); 4.54(t, 1H);                                                      4.28-4.10(m, 2H);                                                              3.83(s, 3H); 3.57(dd, 1H);                                                     3.38(dd, 1H); 1.25(t, 3H)                  Ic.048                                                                             CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                        Ic.049                                                                             CH.sub.2CH(Br)CONH.sub.2                                                   Ic.050                                                                             CH.sub.2CH(Br)CONHCH.sub.3                                                 Ic.051                                                                             CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                          Ic.052                                                                             CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                         Ic.053                                                                             CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                         Ic.054                                                                             CHCH-(4-fluorophenyl)           7.85-6.44(m, 9H);                                                              3.85 and 3.75(2s,                                                              together 3H)                               Ic.055                                                                             CHCH-(4-chlorophenyl)           7.50-6.45(m, 9H);                                                              3.85 and 3.77(2s,                                                              together 3H)                               Ic.056                                                                             CHCH-(3-trifluoromethylphenyl)  480 M!.sup.+                               Ic.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Ic.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Ic.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3     8.25(d, 1H); 8.05(s, 1H);                                                      7.33(d, 1H); 6.73(t, 1H);                                                      3.86(s, 3H); 1.60(s, 9H)                   Ic.060                                                                             CHC(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ic.061                                                                             CHC(Cl)CONHCH.sub.2COOCH.sub.3                                             Ic.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                        8.05(m, 1H);                                                                   7.34-7.02(m, 2H);                                                              6.70(t, 1H); 4.21(s, 2H);                                                      3.85(s, 3H); 3.79(s, 3H);                                                      3.24 and 3.09                                                                  (2s, together 3H);                         Ic.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Ic.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Ic.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Ic.066                                                                             CHC(Cl)CONHOCH.sub.2CHCHCl                                                 Ic.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ic.068                                                                             CHC(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                       Ic.069                                                                             CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                          Ic.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Ic.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Ic.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Ic.073                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.3                                             Ic.074                                                                             CHC(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ic.075                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                      Ic.076                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ic.077                                                                             CHC(Br)COO-cyclohexyl                                                      Ic.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Ic.079                                                                             CHC(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                       Ic.080                                                                             CHC(Br)CONHCH.sub.2COOCH.sub.3                                             Ic.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                        8.00(m, 1H);                                                                   7.33-7.16(m, 2H);                                                              6.71(t, 1H); 4.24(s, 2H);                                                      3.85(s, 3H); 3.79(s, 3H);                                                      3.23 and 3.08                                                                  (2s, together 3H)                          Ic.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Ic.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Ic.084                                                                             CHC(Br)CONHOCH.sub.2CHCHCl                                                 Ic.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ic.086                                                                             CHC(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                       Ic.087                                                                             CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                          Ic.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Ic.089                                                                             CHC(Br)OCH.sub.2CHNOCH.sub.2CHCH.sub.2                                     Ic.090                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ic.091                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.3                                             Ic.092                                                                             CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Ic.093                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                      Ic.094                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                                     Ic.095                                                                             CH.sub.2CH(Cl)COO-cyclohexyl    7.48(d, 1H); 7.24(d, 1H);                                                      6.72(t, 1H); 4.78(m, 1H);                                                      4.56(t, 1H); 3.83(s, 3H);                                                      3.50(dd, 1H); 3.31(dd, 1H);                                                    1.90-1.20(m, 10H)                          Ic.096                                                                             CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                                                             7.50(d, 1H); 7.25(d, 1H);                                                      6.71(t, 1H); 4.48(t, 1H);                                                      3.83(s, 3H); 3.48(dd, 1H);                                                     3.27(dd, 1H); 1.42(s, 9H)                  Ic.097                                                                             CH.sub.2CH(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                Ic.098                                                                             CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                      Ic.099                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                 7.77(m, 1H); 7.50(m, 1H);                                                      6.71(t, 1H); 4.81(s, 2H);                                                      4.50(t, 1H); 3.85(s, 9H);                                                      3.47(dd, 1H); 3.25(dd, 1H)                 Ic.100                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                           Ic.101                                                                             CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                         Ic.102                                                                             CH.sub.2CH(Cl)CONHOCH.sub.3                                                Ic.103                                                                             CH.sub.2CH(Cl)CONHOCH.sub.2CHCHCl                                          Ic.104                                                                             CH.sub.2CH(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                              Ic.105                                                                             CH.sub.2CH(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                Ic.106                                                                             CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                   Ic.107                                                                             CH.sub.2CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                                Ic.108                                                                             CH.sub.2C(Cl)(COOC.sub.2 H.sub.5).sub.2                                    Ic.109                                                                             CHC(Cl)(COOCH.sub.3).sub.2                                                 Ic.110                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.3                                      Ic.111                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Ic.112                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5               Ic.113                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ic.114                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ic.115                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                Ic.116                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ic.117                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                 Ic.118                                                                             CH.sub.2CH(Cl)COOH              8.50(s, 1H); 7,48(d, 1H);                                                      7,29(d, 1H); 6,73(t, 1H);                                                      4,67(dd, 1H); 3,89(s, 3H);                                                     3,55(dd, 1H); 3,30(dd, 1H)                 Ic.119                                                                             CH.sub.2CH(Cl)CONH-cyclopropyl                                             Ic.120                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                      Ic.121                                                                             CH.sub.2CH(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                     7.50(m, 1H); 7.26(d, 1H);                                                      6.93 (m, 1H); 6.70(t, 1H);                                                     4.65(dd, 1H); 4.52(dd, 1H);                                                    4.28-4,13(m, 2H);                                                              3.84(s, 3H); 3.76(m, 1H);                                                      3.19(m, 1H); 2.19(m, 1H);                                                      1.30(m, 3H); 0.90(m, 6H)                   Ic.122                                                                             CH.sub.2CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3               Ic.123                                                                             CH.sub.2CH(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                       Ic.124                                                                             CH.sub.2CH(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                             Ic.125                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ic.126                                                                             CH.sub.2CH(Cl)CON(CN)-cyclopropyl                                          Ic.127                                                                             CH.sub.2CH(Cl)CON(CN)CH.sub.2CHCH.sub.2                                    Ic.128                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ic.129                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)-cyclopropyl                                  Ic.130                                                                             CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ic.131                                                                             CH.sub.2CH(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                          Ic.132                                                                             CH.sub.2CH(Br)COO-cyclohexyl                                               Ic.133                                                                             CH.sub.2CH(Br)COOC(CH.sub.3).sub.3                                                                             7.50(d, 1H); 7.25(d, 1H);                                                      6.72(t, 1H); 4.47(t, 1H);                                                      3.83(s, 3H); 3.52(dd, 1H);                                                     3.35(dd, 1H); 1.42(s, 9H)                  Ic.134                                                                             CH.sub.2CH(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                Ic.135                                                                             CH.sub.2CH(Br)CONHCH.sub.2COOCH.sub.3                                      Ic.136                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                                                 546 M+H!.sup.+,                                                                510 M-Cl!.sup.+                            Ic.137                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                           Ic.138                                                                             CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                         Ic.139                                                                             CH.sub.2CH(Br)CONHOCH.sub.3                                                Ic.140                                                                             CH.sub.2CH(Br)CONHOCH.sub.2CHCHCl                                          Ic.141                                                                             CH.sub.2CH(Br)CONHOCH.sub.2 -(4-chlorophenyl)                              Ic.142                                                                             CH.sub.2CH(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                Ic.143                                                                             CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                   Ic.144                                                                             CH.sub.2CH(Br)COSCH.sub.2 -(4-chlorophenyl)                                Ic.145                                                                             CH.sub.2C(Br)(COOC.sub.2 H.sub.5).sub.2                                    Ic.146                                                                             CH.sub.2C(Br)(COOCH.sub.3).sub.2                                           Ic.147                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.3                                      Ic.148                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Ic.149                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5               Ic.150                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                              Ic.151                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                            Ic.152                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                Ic.153                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                    Ic.154                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                 Ic.155                                                                             CH.sub.2CH(Br)COOH              9.50(s, 1H); 7.48(d, 1H);                                                      7.28(d, 1H); 6.74(t, 1H);                                                      4.61(t, 1H); 3.88(s, 3H);                                                      3.58(dd, 1H); 3.40(dd, 1H)                 Ic.156                                                                             CH.sub.2CH(Br)CONH-cyclopropyl                                             Ic.157                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                      Ic.158                                                                             CH.sub.2CH(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                                     7.50(d, 1H); 7.23(d, 1H);                                                      6.70(t, 1H); 6.61(d, 1H);                                                      4.65-4.45(m, 2H);                                                              4.28-4.10(m, 2H);                                                              3.85(s, 3.H); 3.72(m, 1H);                                                     3.32(m, 1H); 2.15(m, 1H);                                                      1.10(m, 3H);                                                                   1.00-0.80(m, 6H)                           Ic.159                                                                             CH.sub.2CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3               Ic.160                                                                             CH.sub.2CH(Br)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                       Ic.161                                                                             CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                             Ic.162                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ic.163                                                                             CH.sub.2CH(Br)CON(CN)-cyclopropyl                                          Ic.164                                                                             CH.sub.2CH(Br)CON(CN)CH.sub.2CHCH.sub.2                                    Ic.165                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5              Ic.166                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)-cyclopropyl                                  Ic.167                                                                             CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                            Ic.168                                                                             CH.sub.2CH(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                          Ic.169                                                                             CH.sub.2CH(OH)COOH                                                         Ic.170                                                                             CH.sub.2CH(OH)COOCH.sub.3                                                  Ic.171                                                                             CH.sub.2CH(OH)COOC.sub.2 H.sub.5                                           Ic.172                                                                             CH.sub.2CH(OH)COOCH.sub.2CHNOCH.sub.3                                      Ic.173                                                                             CH.sub.2CH(OH)COOC(CH.sub.3).sub.3                                         Ic.174                                                                             CH.sub.2CH(OH)CONH.sub.2                                                   Ic.175                                                                             CH.sub.2CH(OH)CONHCH.sub.3                                                 Ic.176                                                                             CH.sub.2CH(OH)CONH-cyclopropyl                                             Ic.177                                                                             CH.sub.2CH(OCH.sub.3)COOH                                                  Ic.178                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.3                                           Ic.179                                                                             CH.sub.2CH(OCH.sub.3)COOC.sub.2 H.sub.5                                    Ic.180                                                                             CH.sub.2CH(OCH.sub.3)COOCH.sub.2CHNOCH.sub.3                               Ic.181                                                                             CH.sub.2CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                  Ic.182                                                                             CH.sub.2CH(OCH.sub.3)CONH.sub.2                                            Ic.183                                                                             CH.sub.2CH(OCH.sub.3)CONHCH.sub.3                                          Ic.184                                                                             CH.sub.2CH(OCH.sub.3)CONH-cyclopropyl                                      Ic.185                                                                             CH.sub.2CH(OCOCH.sub.3)COOH                                                Ic.186                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.3                                         Ic.187                                                                             CH.sub.2CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                  Ic.188                                                                             CH.sub.2CH(OCOCH.sub.3)COOCH.sub.2CHNOCH.sub.3                             Ic.189                                                                             CH.sub.2CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                                Ic.190                                                                             CH.sub.2CH(OCOCH.sub.3)CONH.sub.2                                          Ic.191                                                                             CH.sub.2CH(OCOCH.sub.3)CONHCH.sub.3                                        Ic.192                                                                             CH.sub.2CH(OCOCH.sub.3)CONH-cyclopropyl                                    Ic.193                                                                             CH.sub.2CH(NH.sub.2)COOH                                                   Ic.194                                                                             CH.sub.2CH(NH.sub.2)COOCH.sub.3                                            Ic.195                                                                             CH.sub.2CH(NH.sub.2)COOC.sub.2 H.sub.5                                     Ic.196                                                                             CH.sub.2CH(NH.sub.2)COOC(CH.sub.3).sub.3                                   Ic.197                                                                             CH.sub.2CH(NH.sub.2)CONH.sub.2                                             Ic.198                                                                             CH.sub.2CH(NH.sub.2)CONHCH.sub.3                                           Ic.199                                                                             CH.sub.2CH(N.sub.3)COOH                                                    Ic.200                                                                             CH.sub.2CH(N.sub.3)COOCH.sub.3                                             Ic.201                                                                             CH.sub.2CH(N.sub.3)COOC.sub.2 H.sub.5                                      Ic.202                                                                             CH.sub.2CH(N.sub.3)COOC(CH.sub.3)3                                         Ic.203                                                                             CH.sub.2CH(N.sub.3)CONH.sub.2                                              Ic.204                                                                             CH.sub.2CH(N.sub.3)CONHCH.sub.3                                            Ic.205                                                                             CH.sub.2CH(NHCOCH.sub.3)COOH                                               Ic.206                                                                             CH.sub.2CH(NHCOCH.sub.3)COOCH.sub.3                                        Ic.207                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                 Ic.208                                                                             CH.sub.2CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                               Ic.209                                                                             CH.sub.2CH(NHCOCH.sub.3)CONH.sub.2                                         Ic.210                                                                             CH.sub.2CH(NHCOCH.sub.3)CONHCH.sub.3                                       Ic.211                                                                             CH.sub.2CH.sub.2 -cyclohexyl                                               Ic.212                                                                             CH.sub.2CH.sub.2 -cyclopentyl                                              Ic.213                                                                             CH.sub.2CH.sub.2 -cyclopropyl                                              Ic.214                                                                             CH.sub.2CH.sub.2 -phenyl                                                   Ic.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Ic.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Ic.217                                                                             CHC(CN)COOC(CH.sub.3)3                                                     Ic.218                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                   Ic.219                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                       Ic.220                                                                             CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                           Ic.221                                                                             CHC(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                        Ic.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                                 Ic.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Ic.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                                 8.06(m, 1H);                                                                   7.35-7.05(m, 2H);                                                              6.72(t, 1H);                                                                   4.30-4.15(m, 4H);                                                              3.85(s, 3H);                                                                   3.25 and 3.10                                                                  (2s, together 3H);                                                             1.30(m, 3H)                                Ic.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ic.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ic.227                                                                             CHC(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                              Ic.228                                                                             CHC(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                                    Ic.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                             Ic.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Ic.231                                                                             CHC(Cl)CON(CN)CH.sub.2CHCH.sub.2                                           Ic.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ic.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Ic.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                   Ic.235                                                                             CHC(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                           Ic.236                                                                             CHC(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                        Ic.237                                                                             CHC(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                                 Ic.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Ic.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                                                                 7.98(m, 1H);                                                                   7.35-7.18(m, 2H);                                                              6.73(t, 1H);                                                                   4.30-4.15(m, 4H);                                                              3.86(s, 3H); 3.24 and 3.10                                                     (2s, together 3H);                                                             1.30(m, 3H)                                Ic.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)CHOC.sub.2 H.sub.5                        Ic.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                      Ic.242                                                                             CHC(Br)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                              Ic.243                                                                             CHC(Br)CONH-(tetrahydrofuran-2-on-3-yl)                                    Ic.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                             Ic.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Ic.246                                                                             CHC(Br)CON(CN)CH.sub.2CHCH.sub.2                                           Ic.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                     Ic.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Ic.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                   Ic.250                                                                             CH.sub.2CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                   Ic.251                                                                             CH.sub.2CH(Br)CON(C.sub.2 H.sub.5).sub.2                                   Ic.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ic.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ic.254                                                                              ##STR70##                                                                 Ic.255                                                                              ##STR71##                                                                 Ic.256                                                                              ##STR72##                                                                 Ic.257                                                                              ##STR73##                                                                 Ic.258                                                                              ##STR74##                                                                 Ic.259                                                                              ##STR75##                                                                 Ic.260                                                                              ##STR76##                                                                 Ic.261                                                                              ##STR77##                                                                 Ic.262                                                                              ##STR78##                                                                 __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR79##                                                                                                 m.p./.sup.1 H-NMR ppm!                             No. R.sup.1                 MS mz.sup.-1 !                                     __________________________________________________________________________     Id.001                                                                             CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                           Id.002                                                                             CH.sub.2CH(CN)CONH.sub.2                                                   Id.003                                                                             CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                          Id.004                                                                             CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                           Id.005                                                                             CH.sub.2CH(Cl)CONH.sub.2                                                   Id.006                                                                             CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                          Id.007                                                                             CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                           Id.008                                                                             CH.sub.2CH(Br)COOCH.sub.3                                                  Id.009                                                                             CH.sub.2CH(Br)CONH.sub.2                                                   Id.010                                                                             CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                          Id.011                                                                             CHC(Cl)COOH                                                                Id.012                                                                             CHC(Cl)COOCH.sub.3                                                         Id.013                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Id.014                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Id.015                                                                             CHC(Br)COOH                                                                Id.016                                                                             CHC(Br)COOCH.sub.3                                                         Id.017                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Id.018                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Id.019                                                                             CHC(Cl)CONH.sub.2                                                          Id.020                                                                             CHC(Cl)CONHCH.sub.3                                                        Id.021                                                                             CHC(Br)CONH.sub.3                                                          Id.022                                                                             CHC(Br)CONHCH.sub.3                                                        Id.023                                                                             CH(cyclohexylene)                                                          Id.024                                                                              ##STR80##                                                                 Id.025                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Id.026                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Id.027                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Id.028                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Id.029                                                                             CHC(CN)COOCH.sub.3                                                         Id.030                                                                             CH.sub.2CH(CN)COOCH.sub.3                                                  Id.031                                                                             CH.sub.2CH(Cl)COOCH.sub.3                                                  Id.032                                                                             CH.sub.2CH(Cl)CONHCH.sub.3                                                 Id.033                                                                             CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                        Id.034                                                                             CH.sub.2CH(Br)CONHCH.sub.3                                                 Id.035                                                                             CHCH-(4-chlorophenyl)                                                      Id.036                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Id.037                                                                             CHC(Cl)CONHCH.sub.2COOCH.sub.3                                             Id.038                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                    Id.039                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Id.040                                                                             CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                          Id.041                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Id.042                                                                             CHC(COOCH.sub.3).sub.2                                                     Id.043                                                                             CHC(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Id.044                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Id.045                                                                             CHC(Br)CONHCH.sub.2COOCH.sub.3                                             Id.046                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                    Id.047                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Id.048                                                                             CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                          Id.049                                                                             CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                      Id.050                                                                             CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                         Id.051                                                                             CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                      Id.052                                                                             CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                             Id.053                                                                             CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                         Id.054                                                                             CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                   Id.055                                                                             CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Id.056                                                                             CH.sub.2CH(Cl)COOH                                                         Id.057                                                                             CH.sub.2CH(Br)COOC(CH.sub.3).sub.3                                         Id.058                                                                             CH.sub.2CH(Br)CONHCH.sub.2COOCH.sub.3                                      Id.059                                                                             CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                             Id.060                                                                             CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                         Id.061                                                                             CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                   Id.062                                                                             CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                               Id.063                                                                             CH.sub.2CH(Br)COOH                                                         Id.064                                                                             CH.sub.2CH(OH)COOH                                                         Id.065                                                                             CH.sub.2CH(OH)COOCH.sub.3                                                  Id.066                                                                             CH.sub.2CH(NH.sub.2)COOH                                                   Id.067                                                                             CH.sub.2CH(NH.sub.2)COOCH.sub.3                                            Id.068                                                                             CH.sub.2CH.sub.2 -cyclohexyl                                               Id.069                                                                             CH.sub.2CH.sub.2 -phenyl                                                   __________________________________________________________________________

                  TABLE 5                                                          ______________________________________                                          ##STR81##                                                                                               m.p./.sup.1 H-NMR  ppm!                              No.    R.sup.1            MS  mz.sup.-1 !                                      ______________________________________                                         Ie.001 CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                       Ie.002 CH.sub.2 CH(CN)CONH.sub.2                                               Ie.003 CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                      Ie.004 CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                       Ie.005 CH.sub.2 CH(Cl)CONH.sub.2                                               Ie.006 CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                      Ie.007 CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                       Ie.008 CH.sub.2 CH(Br)COOCH.sub.3                                              Ie.009 CH.sub.2 CH(Br)CONH.sub.2                                               Ie.010 CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                      Ie.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Ie.012 CHC(Cl)CONH.sub.2                                                       Ie.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Ie.014 CHC(Br)COOC.sub.2 H.sub.5                                               Ie.015 CHC(Br)CONH.sub.2                                                       Ie.016 CHC(Br)CON(CH.sub.3).sub.2                                              Ie.017 CHC(CN)COOC.sub.2 H.sub.5                                               Ie.018 CHC(CN)CONH.sub.2                                                       Ie.019 CHC(CN)CON(CH.sub.3).sub.2                                              Ie.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Ie.021 CHC(CH.sub.3)CONH.sub.2                                                 Ie.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR82##                                                                                               m.p./.sup.1 H-NMR  ppm!                              No.    R.sup.1            MS  mz.sup.-1 !                                      ______________________________________                                         If.001 CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                       If.002 CH.sub.2 CH(CN)CONH.sub.2                                               If.003 CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                      If.004 CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                       If.005 CH.sub.2 CH(Cl)CONH.sub.2                                               If.006 CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                      If.007 CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                       If.008 CH.sub.2 CH(Br)COOCH.sub.3                                              If.009 CH.sub.2 CH(Br)CONH.sub.2                                               If.010 CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                      If.011 CHC(Cl)COOC.sub.2 H.sub.5                                               If.012 CHC(Cl)CONH.sub.2                                                       If.013 CHC(Cl)CON(CH.sub.3).sub.2                                              If.014 CHC(Br)COOC.sub.2 H.sub.5                                               If.015 CHC(Br)CONH.sub.2                                                       If.016 CHC(Br)CON(CH.sub.3).sub.2                                              If.017 CHC(CN)COOC.sub.2 H.sub.5                                               If.018 CHC(CN)CONH.sub.2                                                       If.019 CHC(CN)CON(CH.sub.3).sub.2                                              If.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         If.021 CHC(CH.sub.3)CONH.sub.2                                                 If.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                          ##STR83##                                                                                                m.p./.sup.1 H-NMR  ppm!                             No.   R.sup.1              MS  mz.sup.-1 !                                     ______________________________________                                         Ig.001                                                                               CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                        Ig.002                                                                               CH.sub.2 CH(CN)CONH.sub.2                                                Ig.003                                                                               CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                       Ig.004                                                                               CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                        Ig.005                                                                               CH.sub.2 CH(Cl)CONH.sub.2                                                Ig.006                                                                               CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                       Ig.007                                                                               CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                        Ig.008                                                                               CH.sub.2 CH(Br)COOCH.sub.3                                               Ig.009                                                                               CH.sub.2 CH(Br)CONH.sub.2                                                Ig.010                                                                               CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                       Ig.011                                                                               CHC(Cl)COOC.sub.2 H.sub.5                                                Ig.012                                                                               CHC(Cl)CONH.sub.2                                                        Ig.013                                                                               CHC(Cl)CON(CH.sub.3).sub.2                                               Ig.014                                                                               CHC(Br)COOC.sub.2 H.sub.5                                                Ig.015                                                                               CHC(Br)CONH.sub.2                                                        Ig.016                                                                               CHC(Br)CON(CH.sub.3).sub.2                                               Ig.017                                                                               CHC(CN)COOC.sub.2 H.sub.5                                                Ig.018                                                                               CHC(CN)CONH.sub.2                                                        Ig.019                                                                               CHC(CN)CON(CH.sub.3).sub.2                                               Ig.020                                                                               CHC(CH.sub.3)COOC.sub.2 H.sub.5                                          Ig.021                                                                               CHC(CH.sub.3)CONH.sub.2                                                  Ig.022                                                                               CHC(CH.sub.3)CON(CH.sub.3).sub.2                                         ______________________________________                                    

                                      TABLE 8                                      __________________________________________________________________________      ##STR84##                                                                                                      m.p./.sup.1 H-NMR  ppm!                       No. R.sup.1                      MS  mz.sup.-1 !                               __________________________________________________________________________     Ih.001                                                                             CHC(Cl)COOH                                                                Ih.002                                                                             CHC(Cl)COOCH.sub.3                                                         Ih.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Ih.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Ih.005                                                                             CHC(Br)COOH                                                                Ih.006                                                                             CHC(Br)COOCH.sub.3                                                         Ih.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ih.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ih.009                                                                             CHC(Cl)CONH.sub.2                                                          Ih.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ih.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ih.012                                                                             CHC(Br)CONH.sub.2                                                          Ih.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ih.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Ih.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ih.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Ih.017                                                                             CH(cyclopropylene)                                                         Ih.018                                                                             CH(cyclopentylene)                                                         Ih.019                                                                             CH(cyclohexylene)                                                          Ih.020                                                                              ##STR85##                                                                 Ih.021                                                                              ##STR86##                                                                 Ih.022                                                                              ##STR87##                                                                 Ih.023                                                                              ##STR88##                                                                 Ih.024                                                                              ##STR89##                                                                 Ih.025                                                                              ##STR90##                                                                 Ih.026                                                                              ##STR91##                                                                 Ih.027                                                                              ##STR92##                                                                 Ih.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ih.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ih.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ih.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ih.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ih.033                                                                             CHC(CN)COOCH.sub.3                                                         Ih.034                                                                             CH.sub.2 CH(CN)COOCH.sub.3                                                 Ih.035                                                                             CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                          Ih.036                                                                             CH.sub.2 CH(CN)CONH.sub.2                                                  Ih.037                                                                             CH.sub.2 CH(CN)CONHCH.sub.3                                                Ih.038                                                                             CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                         Ih.039                                                                             CH.sub.2 CH(CN)CONHSO.sub.2 CH.sub.3                                       Ih.040                                                                             CH.sub.2 CH(Cl)COOCH.sub.3   7.94(m, 2H);                                                                   7.72(d, 1H);                                                                   6.70(t, 1H);                                                                   4.46(dd, 1H);                                                                  3.85(s, 3H);                                                                   3.80(s, 3H);                                                                   3.66(dd, 1H);                                                                  3.45(dd, 1H)                                  Ih.041                                                                             CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                                                           7.93(m, 2H);                                                                   7.71(d, 1H);                                                                   6.71(t, 1H);                                                                   4.64(dd, 1H);                                                                  4.26(q, 2H);                                                                   3.84(s, 3H);                                                                   3.66(dd, 1H);                                                                  3.46(dd, 1H);                                                                  1.30(t, 3H)                                   Ih.042                                                                             CH.sub.2 CH(Cl)CONH.sub.2                                                  Ih.043                                                                             CH.sub.2 CH(Cl)CONHCH.sub.3                                                Ih.044                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                         Ih.045                                                                             CH.sub.2 CH(Cl)CONHSO.sub.2 CH.sub.3                                       Ih.046                                                                             CH.sub.2 CH(Br)COOCH.sub.3                                                 Ih.047                                                                             CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                          Ih.048                                                                             CH.sub.2 CH(Br)COOCH(CH.sub.3).sub.2                                       Ih.049                                                                             CH.sub.2 CH(Br)CONH.sub.2                                                  Ih.050                                                                             CH.sub.2 CH(Br)CONHCH.sub.3                                                Ih.051                                                                             CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                         Ih.052                                                                             CH.sub.2 CH(Cl)COCH(CH.sub.3).sub.2                                        IH.053                                                                             CH.sub.2 CH(CN)COCH(CH.sub.3).sub.2                                        Ih.054                                                                             CHCH-(4-fluorophenyl)                                                      Ih.055                                                                             CHCH-(4-chlorophenyl)                                                      Ih.056                                                                             CHCH-(3-trifluoromethylphenyl)                                             Ih.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Ih.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Ih.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Ih.060                                                                             CHC(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Ih.061                                                                             CHC(Cl)CONHCH.sub.2 COOCH.sub.3                                            Ih.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Ih.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Ih.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Ih.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Ih.066                                                                             CHC(Cl)CONHOCH.sub.2 CHCHCl                                                Ih.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ih.068                                                                             CHC(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Ih.069                                                                             CHC(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                         Ih.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Ih.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Ih.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Ih.073                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.3                                            Ih.074                                                                             CHC(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Ih.075                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Ih.076                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Ih.077                                                                             CHC(Br)COO-cyclohexyl                                                      Ih.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Ih.079                                                                             CHC(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Ih.080                                                                             CHC(Br)CONHCH.sub.2 COOCH.sub.3                                            Ih.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Ih.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Ih.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Ih.084                                                                             CHC(Br)CONHOCH.sub.2 CHCHCl                                                Ih.085                                                                             CHC(Br) CONHOCH.sub.2 -(4-chlorophenyl)                                    Ih.086                                                                             CHC(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Ih.087                                                                             CHC(Br)COSCH.sub.2 C.sub.2 H.sub.5                                         Ih.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Ih.089                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Ih.090                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Ih.091                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.3                                            Ih.092                                                                             CHC(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Ih.093                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Ih.094                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Ih.095                                                                             CH.sub.2 CH(Cl)COO-cyclohexyl                                              Ih.096                                                                             CH.sub.2 CH(Cl)COOC(CH.sub.3).sub.3                                        Ih.997                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                              Ih.098                                                                             CH.sub.2 CH(Cl)CONHCH.sub.2 COOCH.sub.3                                    Ih.099                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Ih.100                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Ih.101                                                                             CH.sub.2 CH(Cl)CONHOC.sub.2 H.sub.5                                        Ih.102                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.3                                               Ih.103                                                                             CH.sub.2 CH (Cl)CONHOCH.sub.2 CHCHCl                                       Ih.104                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 -(4-chloro-                                       phenyl)                                                                    Ih.105                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                              Ih.106                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                 Ih.107                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                               Ih.108                                                                             CH.sub.2 C(Cl)(COOC.sub.2 H.sub.5).sub.2                                   Ih.109                                                                             CH.sub.2 C(Cl)(COOCH.sub.3).sub.2                                          Ih.110                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.3                                    Ih.111                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Ih.112                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Ih.113                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Ih.114                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Ih.115                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Ih.116                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Ih.117                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Ih.118                                                                             CH.sub.2 CH(Cl)COOH                                                        Ih.119                                                                             CH.sub.2 CH(Cl)CONH-cyclopropyl                                            Ih.120                                                                             CH.sub.2 CH(Cl) CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                   Ih.121                                                                             CH.sub.2 CH(Cl)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Ih.122                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Ih.123                                                                             CH.sub.2 CH(Cl)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Ih.124                                                                             CH.sub.2 CH(Cl)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Ih.125                                                                             CH.sub.2 CH(Cl)CON(CN)-CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Ih.126                                                                             CH.sub.2 CH(Cl)CON(CN)-cyclopropyl                                         Ih.127                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                  Ih.128                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Ih.129                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)-cyclopropyl                                 Ih.130                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Ih.131                                                                             CH.sub.2 CH(Cl)COO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Ih.132                                                                             CH.sub.2 CH(Br)COO-cyclohexyl                                              Ih.133                                                                             CH.sub.2 CH(Br)COOC(CH.sub.3).sub.3                                        Ih.134                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                              Ih.135                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 COOCH.sub.3                                    Ih.136                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Ih.137                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Ih.138                                                                             CH.sub.2 CH(Br)CONHOC.sub.2 H.sub.5                                        Ih.139                                                                             CH.sub.2 CH(Br)CONHOCH.sub.3                                               Ih.140                                                                             CH.sub.2 CH(Br)CONHOCH.sub.2 CHCHCl                                        Ih.141                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 (4-chloro-                                         phenyl)                                                                    Ih.142                                                                             CH.sub.2 CH(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                              Ih.143                                                                             CH.sub.2 CH(Br)COSCH.sub.2 C.sub.2 H.sub.5                                 Ih.144                                                                             CH.sub.2 CH(Br)COSCH.sub.2 -(4-chlorophenyl)                               Ih.145                                                                             CH.sub.2 C(Br)(COOC.sub.2 H.sub.5).sub.2                                   Ih.146                                                                             CH.sub.2 C(Br)(COOCH.sub.3)2                                               Ih.147                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.3                                    Ih.148                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Ih.149                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Ih.150                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Ih.151                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Ih.152                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Ih.153                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Ih.154                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Ih.155                                                                             CH.sub.2 CH(Br)COOH                                                        Ih.156                                                                             CH.sub.2 CH(Br)CONH-cyclopropyl                                            Ih.157                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Ih.158                                                                             CH.sub.2 CH(Br)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Ih.159                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Ih.160                                                                             CH.sub.2 CH(Br)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Ih.161                                                                             CH.sub.2 CH(Br)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Ih.162                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ih.163                                                                             CH.sub.2 CH(Br)CON(CN)-cyclopropyl                                         Ih.164                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CHCH.sub.2                                  Ih.165                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Ih.166                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)-cyclopropyl                                 Ih.167                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Ih.168                                                                             CH.sub.2 CH(Br)COO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Ih.169                                                                             CH.sub.2 CH(OH)COOH                                                        Ih.170                                                                             CH.sub.2 CH(OH)COOCH.sub.3                                                 Ih.171                                                                             CH.sub.2 CH(OH)COOC.sub.2 H.sub.5                                          Ih.172                                                                             CH.sub.2 CH(OH)COOCH.sub.2 CHNOCH.sub.3                                    Ih.173                                                                             CH.sub.2 CH(OH)COOC(CH.sub.3).sub.3                                        Ih.174                                                                             CH.sub.2 CH(OH)CONH.sub.2                                                  Ih.175                                                                             CH.sub.2 CH(OH)CONHCH.sub.3                                                Ih.176                                                                             CH.sub.2 CH(OH)CONH-cyclopropyl                                            Ih.177                                                                             CH.sub.2 CH(OCH.sub.3)COOH                                                 Ih.178                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                          Ih.179                                                                             CH.sub.2 CH(OCH.sub.3)COOC.sub.2 H.sub.5                                   Ih.180                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                             Ih.181                                                                             CH.sub.2 CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                 Ih.182                                                                             CH.sub.2 CH(OCH.sub.3)CONH.sub.2                                           Ih.183                                                                             CH.sub.2 CH(OCH.sub.3)CONHCH.sub.3                                         Ih.184                                                                             CH.sub.2 CH(OCH.sub.3)CONH-cyclopropyl                                     Ih.185                                                                             CH.sub.2 CH(OCOCH.sub.3)COOH                                               Ih.186                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.3                                        Ih.187                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                 Ih.188                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                           Ih.189                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                               Ih.190                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH.sub.2                                         Ih.191                                                                             CH.sub.2 CH(OCOCH.sub.3)CONHCH.sub.3                                       Ih.192                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH-cyclopropyl                                   Ih.193                                                                             CH.sub.2 CH(NH.sub.2)COOH                                                  Ih.194                                                                             CH.sub.2 CH(NH.sub.2)COOCH.sub.3                                           Ih.195                                                                             CH.sub.2 CH(NH.sub.2)COOC.sub.2 H.sub.5                                    Ih.196                                                                             CH.sub.2 CH(NH.sub.2)COOC(CH.sub.3).sub.3                                  Ih.197                                                                             CH.sub.2 CH(NH.sub.2)CONH.sub.2                                            Ih.198                                                                             CH.sub.2 CH(NH.sub.2)CONHCH.sub.3                                          Ih.199                                                                             CH.sub.2 CH(N.sub.3)COOH                                                   Ih.200                                                                             CH.sub.2 CH(N.sub.3)COOCH.sub.3                                            Ih.201                                                                             CH.sub.2 CH(N.sub.3)COOC.sub.2 H.sub.5                                     Ih.202                                                                             CH.sub.2 CH(N.sub.3)COOC(CH.sub.3).sub.3                                   Ih.203                                                                             CH.sub.2 CH(N.sub.3)CONH.sub.2                                             Ih.204                                                                             CH.sub.2 CH(N.sub.3)CONHCH.sub.3                                           Ih.205                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOH                                              Ih.206                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOCH.sub.3                                       Ih.207                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                Ih.208                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                              Ih.209                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONH.sub.2                                        Ih.210                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONHCH.sub.3                                      Ih.211                                                                             CH.sub.2 CH.sub.2 -cyclohexyl                                              Ih.212                                                                             CH.sub.2 CH.sub.2 -cyclopentyl                                             Ih.213                                                                             CH.sub.2 CH.sub.2 -cyclopropyl                                             Ih.214                                                                             CH.sub.2 CH.sub.2 -phenyl                                                  Ih.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Ih.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Ih.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Ih.218                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Ih.219                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Ih.220                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Ih.221                                                                             CHC(Cl)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Ih.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Ih.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Ih.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Ih.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ih.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Ih.227                                                                             CHC(Cl)CO-(2-methoxycarbonyl-                                                  pyrrolidin-1-yl)                                                           Ih.228                                                                             CHC(Cl)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Ih.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Ih.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Ih.231                                                                             CHC(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                          Ih.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ih.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Ih.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Ih.235                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Ih.236                                                                             CHC(Br)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Ih.237                                                                             CHC(Br)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Ih.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Ih.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Ih.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ih.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Ih.242                                                                             CHC(Br)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Ih.243                                                                             CHC(Br)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Ih.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Ih.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Ih.246                                                                             CHC(Br)CON(CN)CH.sub.2 CHCH.sub.2                                          Ih.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ih.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Ih.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Ih.250                                                                             CH.sub.2 CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                  Ih.251                                                                             CH.sub.2 CH(Br)CON(C.sub.2 H.sub.5).sub.2                                  Ih.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ih.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ih.254                                                                              ##STR93##                                                                 Ih.255                                                                              ##STR94##                                                                 Ih.256                                                                              ##STR95##                                                                 Ih.257                                                                              ##STR96##                                                                 Ih.258                                                                              ##STR97##                                                                 Ih.259                                                                              ##STR98##                                                                 Ih.260                                                                              ##STR99##                                                                 Ih.261                                                                              ##STR100##                                                                Ih.262                                                                              ##STR101##                                                                __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________      ##STR102##                                                                                                     m.p./.sup.1 H-NMR  ppm!                       No. R.sup.1                      MS  mz.sup.-1 !                               __________________________________________________________________________     Ii.001                                                                             CHC(Cl)COOH                                                                Ii.002                                                                             CHC(Cl)COOCH.sub.3                                                         Ii.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Ii.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Ii.005                                                                             CHC(Br)COOH                                                                Ii.006                                                                             CHC(Br)COOCH.sub.3                                                         Ii.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ii.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ii.009                                                                             CHC(Cl)CONH.sub.2                                                          Ii.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ii.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ii.012                                                                             CHC(Br)CONH.sub.2                                                          Ii.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ii.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Ii.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ii.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Ii.017                                                                             CH(cyclopropylene)                                                         Ii.018                                                                             CH(cyclopentylene)                                                         Ii.019                                                                             CH(cyclohexylene)                                                          Ii.020                                                                              ##STR103##                                                                Ii.021                                                                              ##STR104##                                                                Ii.022                                                                              ##STR105##                                                                Ii.023                                                                              ##STR106##                                                                Ii.024                                                                              ##STR107##                                                                Ii.025                                                                              ##STR108##                                                                Ii.026                                                                              ##STR109##                                                                Ii.027                                                                              ##STR110##                                                                Ii.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ii.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ii.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ii.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ii.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ii.033                                                                             CHC(CN)COOCH.sub.3                                                         Ii.034                                                                             CH.sub.2 CH(CN)COOCH.sub.3                                                 Ii.035                                                                             CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                          Ii.036                                                                             CH.sub.2 CH(CN)CONH.sub.2                                                  Ii.037                                                                             CH.sub.2 CH(CN)CONHCH.sub.3                                                Ii.038                                                                             CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                         Ii.039                                                                             CH.sub.2 CH(CN)CONHSO.sub.2 CH.sub.3                                       Ii.040                                                                             CH.sub.2 CH(Cl)COOCH.sub.3                                                 Ii.041                                                                             CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                          Ii.042                                                                             CH.sub.2 CH(Cl)CONH.sub.2                                                  Ii.043                                                                             CH.sub.2 CH(Cl)CONHCH.sub.3                                                Ii.044                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                         Ii.045                                                                             CH.sub.2 CH(Cl)CONHSO.sub.2 CH.sub.3                                       Ii.046                                                                             CH.sub.2 CH(Br)COOCH.sub.3                                                 Ii.047                                                                             CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                          Ii.048                                                                             CH.sub.2 CH(Br)COOCH(CH.sub.3).sub.2                                       Ii.049                                                                             CH.sub.2 CH(Br)CONH.sub.2                                                  Ii.050                                                                             CH.sub.2 CH(Br)CONHCH.sub.3                                                Ii.051                                                                             CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                         Ii.052                                                                             CH.sub.2 CH(Cl)COCH(CH.sub.3).sub.2                                        Ii.053                                                                             CH.sub.2 CH(CN)COCH(CH.sub.3).sub.2                                        Ii.054                                                                             CHCH-(4-fluorophenyl)                                                      Ii.055                                                                             CHCH-(4-chlorophenyl)                                                      Ii.056                                                                             CHCH-(3-trifluoromethylphenyl)                                             Ii.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Ii.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Ij.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Ii.060                                                                             CHC(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Ii.061                                                                             CHC(Cl)CONHCH.sub.2 COOCH.sub.3                                            Ii.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Ii.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Ii.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Ii.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Ii.066                                                                             CHC(Cl)CONHOCH.sub.2 CHCHCl                                                Ii.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ii.068                                                                             CHC(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Ii.069                                                                             CHC(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                         Ii.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Ii.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Ii.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Ii.073                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.3                                            Ii.074                                                                             CHC(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Ii.075                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Ii.076                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Ii.077                                                                             CHC(Br)COO-cyclohexyl                                                      Ii.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Ii.079                                                                             CHC(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Ii.080                                                                             CHC(Br)CONHCH.sub.2 COOCH.sub.3                                            Ii.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Ii.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Ii.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Ii.084                                                                             CHC(Br)CONHOCH.sub.2 CHCHCl                                                Ii.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Ii.086                                                                             CHC(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Ii.087                                                                             CHC(Br)COSCH.sub.2 C.sub.2 H.sub.5                                         Ii.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Ii.089                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Ii.090                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Ii.091                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.3                                            Ii.092                                                                             CHC(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Ii.093                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Ii.094                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Ii.095                                                                             CH.sub.2 CH(Cl)COO-cyclohexyl                                              Ii.096                                                                             CH.sub.2 CH(Cl)COOC(CH.sub.3).sub.3                                        Ii.097                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                              Ii.098                                                                             CH.sub.2 CH(Cl)CONHCH.sub.2 COOCH.sub.3                                    Ii.099                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Ii.100                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Ii.101                                                                             CH.sub.2 CH(Cl)CONHOC.sub.2 H.sub.5                                        Ii.102                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.3                                               Ii.103                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 CHCHCl                                        Ii.104                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 -(4-chloro-                                       phenyl)                                                                    Ii.105                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                              Ii.106                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                 Ii.107                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                               Ii.108                                                                             CH.sub.2 C(Cl)(COOC.sub.2 H.sub.5).sub.2                                   Ii.109                                                                             CH.sub.2 C(Cl)(COOCH.sub.3)2                                               Ii.110                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.3                                    Ii.111                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Ii.112                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Ii.113                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Ii.114                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Ii.115                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNHOCH.sub.2 CHCHCl                            Ii.116                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Ii.117                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Ii.118                                                                             CH.sub.2 CH(Cl)COOH                                                        Ii.119                                                                             CH.sub.2 CH(Cl)CONH-cyclopropyl                                            Ii.120                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Ii.121                                                                             CH.sub.2 CH(Cl)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Ii.122                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Ii.123                                                                             CH.sub.2 CH(Cl)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Ii.124                                                                             CH.sub.2 CH(Cl)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Ii.125                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ii.126                                                                             CH.sub.2 CH(Cl)CON(CN)-cyclopropyl                                         Ii.127                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                  Ii.128                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Ii.129                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)-cyclopropyl                                 Ii.130                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Ii.131                                                                             CH.sub.2 CH(Cl)COO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Ii.132                                                                             CH.sub.2 CH(Br)COO-cyclohexyl                                              Ii.133                                                                             CH.sub.2 CH(Br)COOC(CH.sub.3).sub.3                                        Ii.134                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                              Ii.135                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 COOCH.sub.3                                    Ii.136                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Ii.137                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Ii.138                                                                             CH.sub.2 CH(Br)CONHOC.sub.2 H.sub.5                                        Ii.139                                                                             CH.sub.2 CH(Br.)CONHOCH.sub.3                                              Ii.140                                                                             CH.sub.2 CH(Br)CONHOCH.sub.2 CHCHCl                                        Ii.141                                                                             CH.sub.2 CH(Br)CONHCH.sub.2                                                    (4-chlorophenyl)                                                           Ii.142                                                                             CH.sub.2 CH(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                              Ii.143                                                                             CH.sub.2 CH(Br)COSCH.sub.2 C.sub.2 H.sub.5                                 Ii.144                                                                             CH.sub.2 CH(Br)COSCH.sub.2 -(4-chlorophenyl)                               Ii.145                                                                             CH.sub.2 C(Br)(COOC.sub.2 H.sub.5).sub.2                                   Ii.146                                                                             CH.sub.2 C(Br)(COOCH.sub.3)2                                               Ii.147                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.3                                    Ii.148                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Ii.149                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Ii.150                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Ii.151                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Ii.152                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Ii.153                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Ii.154                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Ii.155                                                                             CH.sub.2 CH(Br)COOH                                                        Ii.156                                                                             CH.sub.2 CH(Br)CONH-cyclopropyl                                            Ii.157                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Ii.158                                                                             CH.sub.2 CH(Br)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Ii.159                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Ii.160                                                                             CH.sub.2 CH(Br)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Ii.161                                                                             CH.sub.2 CH(Br)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Ii.162                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ii.163                                                                             CH.sub.2 CH(Br)CON(CN)-cyclopropyl                                         Ii.164                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CHCH.sub.2                                  Ii.165                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Ii.166                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)-cyclopropyl                                 Ii.167                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Ii.168                                                                             CH.sub.2 CH(Br)COO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Ii.169                                                                             CH.sub.2 CH(OH)COOH                                                        Ii.170                                                                             CH.sub.2 CH(OH)COOCH.sub.3                                                 Ii.171                                                                             CH.sub.2 CH(OH)COOC.sub.2 H.sub.5                                          Ii.172                                                                             CH.sub.2 CH(OH)COOCH.sub.2 CHNOCH.sub.3                                    Ii.173                                                                             CH.sub.2 CH(OH)COOC(CH.sub.3).sub.3                                        Ii.174                                                                             CH.sub.2 CH(OH)CONH.sub.2                                                  Ii.175                                                                             CH.sub.2 CH(OH)CONHCH.sub.3                                                Ii.176                                                                             CH.sub.2 CH(OH)CONH-cyclopropyl                                            Ii.177                                                                             CH.sub.2 CH(OCH.sub.3)COOH                                                 Ii.178                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                          Ii.179                                                                             CH.sub.2 CH(OCH.sub.3)COOC.sub.2 H.sub.5                                   Ii.180                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                             Ii.181                                                                             CH.sub.2 CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                 Ii.182                                                                             CH.sub.2 CH(OCH.sub.3)CONH.sub.2                                           Ii.183                                                                             CH.sub.2 CH(OCH.sub.3)CONHCH.sub.3                                         Ii.184                                                                             CH.sub.2 CH(OCH.sub.3)CONH-cyclopropyl                                     Ii.185                                                                             CH.sub.2 CH(OCOCH.sub.3)COOH                                               Ii.186                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.3                                        Ii.187                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                 Ii.188                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                           Ii.189                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                               Ii.190                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH.sub.2                                         Ii.191                                                                             CH.sub.2 CH(OCOCH.sub.3)CONHCH.sub.3                                       Ii.192                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH-cyclopropyl                                   Ii.193                                                                             CH.sub.2 CH(NH.sub.2)COOH                                                  Ii.194                                                                             CH.sub.2 CH(NH.sub.2)COOCH.sub.3                                           Ii.195                                                                             CH.sub.2 CH(NH.sub.2)COOC.sub.2 H.sub.5                                    Ii.196                                                                             CH.sub.2 CH(NH.sub.2)COOC(CH.sub.3).sub.3                                  Ii.197                                                                             CH.sub.2 CH(NH.sub.2)CONH.sub.2                                            Ii.198                                                                             CH.sub.2 CH(NH.sub.2)CONHCH.sub.3                                          Ii.199                                                                             CH.sub.2 CH(N.sub.3)COOH                                                   Ii.200                                                                             CH.sub.2 CH(N.sub.3)COOCH.sub.3                                            Ii.201                                                                             CH.sub.2 CH(N.sub.3)COOC.sub.2 H.sub.5                                     Ii.202                                                                             CH.sub.2 CH(N.sub.3)COOC(CH.sub.3).sub.3                                   Ii.203                                                                             CH.sub.2 CH(N.sub.3)CONH.sub.2                                             Ii.204                                                                             CH.sub.2 CH(N.sub.3)CONHCH.sub.3                                           Ii.205                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOH                                              Ii.206                                                                             CHzCH(NHCOCH.sub.3)COOCH.sub.3                                             Ii.207                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                Ii.208                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                              Ii.209                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONH.sub.2                                        Ii.210                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONHCH.sub.3                                      Ii.211                                                                             CH.sub.2 CH.sub.2 -cyclohexyl                                              Ii.212                                                                             CH.sub.2 CH.sub.2 -cyclopentyl                                             Ii.213                                                                             CH.sub.2 CH.sub.2 -cyclopropyl                                             Ii.214                                                                             CH.sub.2 CH.sub.2 -phenyl                                                  Ii.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Ii.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Ii.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Ii.218                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Ii.219                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Ii.220                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Ii.221                                                                             CHC(Cl)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Ii.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Ii.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Ii.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Ii.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ii.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Ii.227                                                                             CHC(Cl)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Ii.228                                                                             CHC(Cl)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Ii.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Ii.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Ii.231                                                                             CHC(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                          Ii.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ii.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Ii.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Ii.235                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Ii.236                                                                             CHC(Br)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Ii.237                                                                             CHC(Br)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Ii.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Ii.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Ii.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Ii.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Ii.242                                                                             CHC(Br)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Ii.243                                                                             CHC(Br)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Ii.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Ii.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Ii.246                                                                             CHC(Br)CON(CN)CH.sub.2 CHCH.sub.2                                          Ii.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Ii.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Ii.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Ii.250                                                                             CH.sub.2 CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                  Ii.251                                                                             CH.sub.2 CH(Br)CON(C.sub.2 H.sub.5).sub.2                                  Ii.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ii.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ii.254                                                                              ##STR111##                                                                Ii.255                                                                              ##STR112##                                                                Ii.256                                                                              ##STR113##                                                                Ii.257                                                                              ##STR114##                                                                Ii.258                                                                              ##STR115##                                                                Ii.259                                                                              ##STR116##                                                                Ii.260                                                                              ##STR117##                                                                Ii.261                                                                              ##STR118##                                                                Ii.262                                                                              ##STR119##                                                                __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR120##                                                                                                            m.p./.sup.1 H-NMR ppm!                 No.                                                                               R.sup.1                              MS  mz.sup.-1 !                        __________________________________________________________________________     Ij.001                                                                            CHC(Cl)COOH                                                                 Ij.002                                                                            CHC(Cl)COOCH.sub.3                                                          Ij.003                                                                            CHC(Cl)COOC.sub.2 H.sub.5                                                   Ij.004                                                                            CHC(Cl)COOCH(CH.sub.3).sub.2                                                Ij.005                                                                            CHC(Br)COOH                                                                 Ij.006                                                                            CHC(Br)COOCH.sub.3                                                          Ij.007                                                                            CHC(Br)COOC.sub.2 H.sub.5                                                   Ij.008                                                                            CHC(Br)COOCH(CH.sub.3).sub.2                                                Ij.009                                                                            CHC(Cl)CONH.sub.2                                                           Ij.010                                                                            CHC(Cl)CONHCH.sub.3                                                         Ij.011                                                                            CHC(Cl)CON(CH.sub.3).sub.2                                                  Ij.012                                                                            CHC(Br)CONH.sub.2                                                           Ij.013                                                                            CHC(Br)CONHCH.sub.3                                                         Ij.014                                                                            CHC(Br)CON(CH.sub.3).sub.2                                                  Ij.015                                                                            CHC(Br)CONH-cyclopropyl                                                     Ij.016                                                                            CHC(Cl)CONH-cyclopropyl                                                     Ij.017                                                                            CH(cyclopropylene)                                                          Ij.018                                                                            CH(cyclopentylene)                                                          Ij.019                                                                            CH(cyclohexylene)                                                           Ij.020                                                                             ##STR121##                                                                 Ij.021                                                                             ##STR122##                                                                 Ij.022                                                                             ##STR123##                                                                 Ij.023                                                                             ##STR124##                                                                 Ij.024                                                                             ##STR125##                                                                 Ij.025                                                                             ##STR126##                                                                 Ij.026                                                                             ##STR127##                                                                 Ij.027                                                                             ##STR128##                                                                 Ij.028                                                                            CHC(CH.sub.3)COOC.sub.2 H.sub.5                                             Ij.029                                                                            CHC(CH.sub.3)COOCH.sub.3                                                    Ij.030                                                                            CHC(CH.sub.3)CONH.sub.2                                                     Ij.031                                                                            CHC(CH.sub.3)CONHCH.sub.3                                                   Ij.032                                                                            CHC(CH.sub.3)CON(CH.sub.3).sub.2                                            Ij.033                                                                            CHC(CN)COOCH.sub.3                                                          Ij.034                                                                            CH.sub.2CH(CN)COOCH.sub.3                                                   Ij.035                                                                            CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                            Ij.036                                                                            CH.sub.2CH(CN)CONH.sub.2                                                    Ij.037                                                                            CH.sub.2CH(CN)CONHCH.sub.3                                                  Ij.038                                                                            CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                           Ij.039                                                                            CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                          Ij.040                                                                            CH.sub.2CH(Cl)COOCH.sub.3                                                   Ij.041                                                                            CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                            Ij.042                                                                            CH.sub.2CH(Cl)CONH.sub.2                                                    Ij.043                                                                            CH.sub.2CH(Cl)CONHCH.sub.3                                                  Ij.044                                                                            CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                           Ij.045                                                                            CH.sub.2CH(Cl)CONHSO.sub.2 CH.sub.3                                         Ij.046                                                                            CH.sub.2CH(Br)COOCH.sub.3                                                   Ij.047                                                                            CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                            Ij.048                                                                            CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                         Ij.049                                                                            CH.sub.2CH(Br)CONH.sub.2                                                    Ij.050                                                                            CH.sub.2CH(Br)CONHCH.sub.3                                                  Ij.051                                                                            CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                           Ij.052                                                                            CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                          Ij.053                                                                            CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                          Ij.054                                                                            CHCH-(4-fluorophenyl)                                                       Ij.055                                                                            CHCH-(4-chlorophenyl)                                                       Ij.056                                                                            CHCH-(3-trifluoromethylphenyl)                                              Ij.057                                                                            CHCH-(2,4-dichlorophenyl)                                                   Ij.058                                                                            CHC(Cl)COO-cyclohexyl                                                       Ij.059                                                                            CHC(Cl)COOC(CH.sub.3).sub.3                                                 Ij.060                                                                            CHC(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                        Ij.061                                                                            CHC(Cl)CONHCH.sub.2COOCH.sub.3                                              Ij.062                                                                            CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                     Ij.063                                                                            CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                   Ij.064                                                                            CHC(Cl)CONHOC.sub.2 H.sub.5                                                 Ij.065                                                                            CHC(Cl)CONHOCH.sub.3                                                        Ij.066                                                                            CHC(Cl)CONHOCH.sub.2 CHCHCl                                                 Ij.067                                                                            CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                      Ij.068                                                                            CHC(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                        Ij.069                                                                            CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                           Ij.070                                                                            CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                        Ij.071                                                                            CHC(COOC.sub.2 H.sub.5).sub.2                                               Ij.072                                                                            CHC(COOCH.sub.3).sub.2                                                      Ij.073                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.3                                              Ij.074                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2 H.sub.5                                      Ij.075                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                       Ij.076                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2phenyl                                        Ij.077                                                                            CHC(Br)COO-cyclohexyl                                                       Ij.078                                                                            CHC(Br)COOC(CH.sub.3).sub.3                                                 Ij.079                                                                            CHC(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                        Ij.080                                                                            CHC(Br)CONHCH.sub.2COOCH.sub.3                                              Ij.081                                                                            CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                     Ij.082                                                                            CHC(Br)CONHOC.sub.2 H.sub.5                                                 Ij.083                                                                            CHC(Br)CONHOCH.sub.3                                                        Ij.084                                                                            CHC(Br)CONHOCH.sub.2CHCHCl                                                  Ij.085                                                                            CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                      Ij.086                                                                            CHC(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                        Ij.087                                                                            CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                           Ij.088                                                                            CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                        Ij.089                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                    Ij.090                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                        Ij.091                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.3                                              Ij.092                                                                            CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                       Ij.093                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                       Ij.094                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                                      Ij.095                                                                            CH.sub.2CH(Cl)COOcyclohexyl                                                 Ij.096                                                                            CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                          Ij.097                                                                            CH.sub.2CH(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                 Ij.098                                                                            CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                       Ij.099                                                                            CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                              Ij.100                                                                            CH.sub.2CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                            Ij.101                                                                            CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                          Ij.102                                                                            CH.sub.2CH(Cl)CONHOCH.sub.3                                                 Ij.103                                                                            CH.sub.2CH(Cl)CONHOCH.sub.2CHCHCl                                           Ij.104                                                                            CH.sub.2CH(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                               Ij.105                                                                            CH.sub.2CH(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                 Ij.106                                                                            CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                    Ij.107                                                                            CH.sub.2CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                                 Ij.108                                                                            CH.sub.2C(Cl)(COOC.sub.2 H.sub.5).sub.2                                     Ij.109                                                                            CH.sub.2C(Cl)(COOCH.sub.3).sub.2                                            Ij.110                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.3                                       Ij.111                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                Ij.112                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                Ij.113                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                               Ij.114                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                             Ij.115                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                 Ij.116                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                     Ij.117                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                  Ij.118                                                                            CH.sub.2CH(Cl)COOH                                                          Ij.119                                                                            CH.sub.2CH(Cl)CONH-cyclopropyl                                              Ij.120                                                                            CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COCO.sub.2 H.sub.5                       Ij.121                                                                            CH.sub.2CH(Cl)CONHCH(CH)CH.sub.3).sub.2)COOC.sub.2 H.sub.5                  Ij.122                                                                            CH.sub.2CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                Ij.123                                                                            CH.sub.2CH(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                        Ij.124                                                                            CH.sub.2CH(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.125                                                                            CH.sub.2CH(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                       Ij.126                                                                            CH.sub.2CH(Cl)CON(CN)-cyclopropyl                                           Ij.127                                                                            CH.sub.2CH(Cl)CON(CN)CH.sub.2CHCH.sub.2                                     Ij.128                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5               Ij.129                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)-cyclopropyl                                   Ij.130                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                            Ij.131                                                                            CH.sub.2CH(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                           Ij.132                                                                            CH.sub.2CH(Br)COO-cyclohexyl                                                Ij.133                                                                            CH.sub.2CH(Br)COOC(CH.sub.3).sub.3                                          Ij.134                                                                            CH.sub.2CH(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                 Ij.135                                                                            CH.sub.2CH(Br)CONHCH.sub.2 COOCH.sub.3                                      Ij.136                                                                            CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                              Ij.137                                                                            CH.sub.2CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                            Ij.138                                                                            CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                          Ij.139                                                                            CH.sub.2CH(Br)CONHOCH.sub.3                                                 Ij.140                                                                            CH.sub.2CH(Br)CONHOCH.sub.2CHCHCl                                           Ij.141                                                                            CH.sub.2CH(Br)CONHCH.sub.2 -(4-chlorophenyl)                                Ij.142                                                                            CH.sub.2CH(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                 Ij.143                                                                            CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                    Ij.144                                                                            CH.sub.2CH(Br)COSCH.sub.2 -(4-chlorophenyl)                                 Ij.145                                                                            CH.sub.2C(Br)(COOC.sub.2 H.sub.5).sub.2                                     Ij.146                                                                            CH.sub.2C(Br)(COOCH.sub.3).sub.2                                            Ij.147                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.3                                       Ij.148                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                Ij.149                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                Ij.150                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                               Ij.151                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                             Ij.152                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                 Ij.153                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                     Ij.154                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                  Ij.155                                                                            CH.sub.2CH(Br)COOH                                                          Ij.156                                                                            CH.sub.2CH(Br)CONH-cyclopropyl                                              Ij.157                                                                            CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                       Ij.158                                                                            CH.sub.2CH(Br)CONHCH(CH(CH.sub.3).sub.2)COOCH.sub.2 H.sub.5                 Ij.159                                                                            CH.sub.2CH(Br)CONHCH(CH.sub.2CH(CH.sub.3).sub.2)COOCH.sub.3                 Ij.160                                                                            CH.sub.2CH(Br)CO-(2-methoxycarbonylpyrrolidin-1-yl)                         Ij.160                                                                            CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.161                                                                            CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.162                                                                            CH.sub.2CH(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                       Ij.163                                                                            CH.sub.2CH(Br)CON(CN)-cyclopropyl                                           Ij.164                                                                            CH.sub.2CH(Br)CON(CN)CH.sub.2CHCH.sub.2                                     Ij.165                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5               Ij.166                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)-cyclopropyl                                   Ij.167                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                             Ij.168                                                                            CH.sub.2CH(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                           Ij.169                                                                            CH.sub.2CH(OH)COOH                                                          Ij.170                                                                            CH.sub.2CH(OH)COOCH.sub.3                                                   Ij.171                                                                            CH.sub.2CH(OH)COOC.sub.2 H.sub.5                                            Ij.172                                                                            CH.sub.2CH(OH)COOCH.sub.2CHNOCH.sub.3                                       Ij.173                                                                            CH.sub.2CH(OH)COOC(CH.sub.3).sub.3                                          Ij.174                                                                            CH.sub.2CH(OH)CONH.sub.2                                                    Ij.175                                                                            CH.sub.2CH(OH)CONHCH.sub.3                                                  Ij.176                                                                            CH.sub.2CH(OH)CONH-cyclopropyl                                              Ij.177                                                                            CH.sub.2CH(OCH.sub.3)COOH                                                   Ij.178                                                                            CH.sub.2CH(OCH.sub.3)COOCH.sub.3                                            Ij.179                                                                            CH.sub.2CH(OCH.sub.3)COOC.sub.2 H.sub.5                                     Ij.180                                                                            CH.sub.2CH(OCH.sub.3)COOCH.sub.2CHNOCH.sub.3                                Ij.181                                                                            CH.sub.2CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                   Ij.182                                                                            CH.sub.2CH(OCH.sub.3)CONH.sub.2                                             Ij.183                                                                            CH.sub.2CH(OCH.sub.3)CONHCH.sub.3                                           Ij.184                                                                            CH.sub.2CH(OCH.sub.3)CONH-cyclopropyl                                       Ij.185                                                                            CH.sub.2CH(OCOCH.sub.3)COOH                                                 Ij.186                                                                            CH.sub.2CH(OCOCH.sub.3)COOCH.sub.3                                          Ij.187                                                                            CH.sub.2CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                   Ij.188                                                                            CH.sub.2CH(OCOCH.sub.3)COOCH.sub.2CHNOCH.sub.3                              Ij.189                                                                            CH.sub.2CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                                 Ij.190                                                                            CH.sub.2CH(OCOCH.sub.3)CONH.sub.2                                           Ij.191                                                                            CH.sub.2CH(OCOCH.sub.3)CONHCH.sub.3                                         Ij.192                                                                            CH.sub.2CH(OCOCH.sub.3)CONH-cyclopropyl                                     Ij.193                                                                            CH.sub.2CH(NH.sub.2)COOH                                                    Ij.194                                                                            CH.sub.2CH(NH.sub.2)COOCH.sub.3                                             Ij.195                                                                            CH.sub.2CH(NH.sub.2)COOC.sub.2 H.sub.5                                      Ij.196                                                                            CH.sub.2CH(NH.sub.2)COOC(CH.sub.3).sub.3                                    Ij.197                                                                            CH.sub.2CH(NH.sub.2)CONH.sub.2                                              Ij.198                                                                            CH.sub.2CH(NH.sub.2)CONHCH.sub.3                                            Ij.199                                                                            CH.sub.2CH(N.sub.3)COOH                                                     Ij.200                                                                            CH.sub.2CH(N.sub.3)COOCH.sub.3                                              Ij.201                                                                            CH.sub.2CH(N.sub.3)COOC.sub.2 H.sub.5                                       Ij.202                                                                            CH.sub.2CH(N.sub.3)COOC(CH.sub.3).sub.3                                     Ij.203                                                                            CH.sub.2CH(N.sub.3)CONH.sub.2                                               Ij.204                                                                            CH.sub.2CH(N.sub.3)CONHCH.sub.3                                             Ij.205                                                                            CH.sub.2CH(NHCOCH.sub.3)COOH                                                Ij.206                                                                            CH.sub.2CH(NHCOCH.sub.3)COOCH.sub.3                                         Ij.207                                                                            CH.sub.2CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                  Ij.208                                                                            CH.sub.2CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                                Ij.209                                                                            CH.sub.2CH(NHCOCH.sub.3)CONH.sub.2                                          Ij.210                                                                            CH.sub.2CH(NHCOCH.sub.3)CONHCH.sub.3                                        Ij.211                                                                            CH.sub.2CH.sub.2cyclohexyl                                                  Ij.212                                                                            CH.sub.2CH.sub.2cyclopentyl                                                 Ij.213                                                                            CH.sub.2CH.sub.2cyclopropyl                                                 Ij.214                                                                            CH.sub.2CH.sub.2phenyl                                                      Ij.215                                                                            CHC(CN)COOC.sub.2 H.sub.5                                                   Ij.216                                                                            CHC(CN)COOCH(CH.sub.3).sub.2                                                Ij.217                                                                            CHC(CN)COOC(CH.sub.3).sub.3                                                 Ij.218                                                                            CHC(CN)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                    Ij.219                                                                            CHC(CN)COOCH.sub.2CHNOCH.sub.2CHCHCl                                        Ij.220                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                            Ij.221                                                                            CHC(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                         Ij.222                                                                            CHC(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                                  Ij.223                                                                            CHC(Cl)CONH-cyclohexyl                                                      Ij.224                                                                            CHC(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                              Ij.225                                                                            CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                         Ij.226                                                                            CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                       Ij.227                                                                            CHC(Cl)CO-(2-methoxycarbonylpyrrolidin-1-yl)                                Ij.228                                                                            CHC(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                                     Ij.229                                                                            CHC(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                              Ij.230                                                                            CHC(Cl)CON(CN)-cyclopropyl                                                  Ij.231                                                                            CHC(Cl)CON(CN)CH.sub.2CHCH.sub.2                                            Ij.232                                                                            CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ij.233                                                                            CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                          Ij.234                                                                            CHC(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                    Ij.235                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                            Ij.236                                                                            CHC(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                         Ij.237                                                                            CHC(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                                  Ij.238                                                                            CHC(Br)CONH-cyclohexyl                                                      Ij.239                                                                            CHC(Br)CON(CH.sub.3)CH.sub.2COCO.sub.2 H.sub.5                              Ij.240                                                                            CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                         Ij.241                                                                            CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                       Ij.242                                                                            CHC(Br)CO-(2-methoxycarbonylpyrrolidin-1-yl)                                Ij.243                                                                            CHC(Br)CONH-(tetrahydrofuran-2-on-3-yl)                                     Ij.244                                                                            CHC(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                              Ij.245                                                                            CHC(Br)CON(CN)-cyclopropyl                                                  Ij.246                                                                            CHC(Br)CON(CN)CH.sub.2CHCH.sub.2                                            Ij.247                                                                            CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ij.248                                                                            CHC(Br)CON(CONH.sub.2)-cyclopropyl                                          Ij.249                                                                            CHC(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                    Ij.250                                                                            CH.sub.2CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                    Ij.251                                                                            CH.sub.2CH(Br)CON(C.sub.2 H.sub.5).sub.2                                    Ij.252                                                                            CHCH(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ij.253                                                                            CHCH(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ij.254                                                                             ##STR129##                                                                 Ij.255                                                                             ##STR130##                                                                 Ij.256                                                                             ##STR131##                                                                 Ij.257                                                                             ##STR132##                                                                 Ij.258                                                                             ##STR133##                                                                 Ij.259                                                                             ##STR134##                                                                 Ij.260                                                                             ##STR135##                                                                 Ij.261                                                                             ##STR136##                                                                 Ij.262                                                                             ##STR137##                                                                 __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR138##                                                                                                   m.p./.sup.1 H-NMR ppm!                          No. R.sup.1                    MS  mz.sup.-1 !                                 __________________________________________________________________________     Ik.001                                                                             CHC(Cl)COOH                                                                Ik.002                                                                             CHC(Cl)COOCH.sub.3                                                         Ik.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Ik.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Ik.005                                                                             CHC(Br)COOH                                                                Ik.006                                                                             CHC(Br)COOCH.sub.3                                                         Ik.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Ik.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Ik.009                                                                             CHC(Cl)CONH.sub.2                                                          Ik.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Ik.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Ik.012                                                                             CHC(Br)CONH.sub.2                                                          Ik.013                                                                             CHC(Br)CONHCH.sub.3                                                        Ik.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Ik.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Ik.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Ik.017                                                                             CH(cyclopropylene)                                                         Ik.018                                                                             CH(cyclopentylene)                                                         Ik.019                                                                             CH(cyclohexylene)                                                          Ik.020                                                                              ##STR139##                                                                Ik.021                                                                              ##STR140##                                                                Ik.022                                                                              ##STR141##                                                                Ik.023                                                                              ##STR142##                                                                Ik.024                                                                              ##STR143##                                                                Ik.025                                                                              ##STR144##                                                                Ik.026                                                                              ##STR145##                                                                Ik.027                                                                              ##STR146##                                                                Ik.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Ik.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Ik.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Ik.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Ik.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Ik.033                                                                             CHC(CN)COOCH.sub.3                                                         Ik.034                                                                             CH.sub.2CH(CN)COOCH.sub.3                                                  Ik.035                                                                             CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                           Ik.036                                                                             CH.sub.2CH(CN)CONH.sub.2                                                   Ik.037                                                                             CH.sub.2CH(CN)CONHCH.sub.3                                                 Ik.038                                                                             CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                          Ik.039                                                                             CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                         Ik.040                                                                             CH.sub.2CH(Cl)COOCH.sub.3                                                  Ik.041                                                                             CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                           Ik.042                                                                             CH.sub.2CH(Cl)CONH.sub.2                                                   Ik.043                                                                             CH.sub.2CH(Cl)CONHCH.sub.3                                                 Ik.044                                                                             CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                          Ik.045                                                                             CH.sub.2CH(Cl)CONHSO.sub.2 CH.sub.3                                        Ik.046                                                                             CH.sub.2CH(Br)COOCH.sub.3                                                  Ik.047                                                                             CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                           Ik.048                                                                             CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                        Ik.049                                                                             CH.sub.2CH(Br)CONH.sub.2                                                   Ik.050                                                                             CH.sub.2CH(Br)CONHCH.sub.3                                                 Ik.051                                                                             CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                          Ik.052                                                                             CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                         Ik.053                                                                             CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                         Ik.054                                                                             CHCH-(4-fluorophenyl)                                                      Ik.055                                                                             CHCH-(4-chlorophenyl)                                                      Ik.056                                                                             CHCH-(3-trifluoromethylphenyl)                                             Ik.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR147##                                                                                                            m.p./.sup.1 H-NMR ppm!                 No.                                                                               R.sup.1                              MS  mz.sup.-1 !                        __________________________________________________________________________     Ij.001                                                                            CHC(Cl)COOH                          8.07(d, 1H);                                                                   7.96(s, 1H);                                                                   7.81(d, 1H);                                                                   7.40(t, 1H);                                                                   3.82(s, 1H);                           Ij.002                                                                            CHC(Cl)COOCH.sub.3                   8.28(d, 1H);                                                                   8.05(s, 1H);                                                                   7.31(d, 1H);                                                                   6.73(t, 1H);                                                                   3.92(s, 3H);                                                                   3.85(s, 3H)                            Ij.003                                                                            CHC(Cl)COOC.sub.2 H.sub.5            8.26(d, 1H);                                                                   8.04(s, 1H);                                                                   7.31(d, 1H);                                                                   6.73(t, 1H);                                                                   4.38(q, 2H);                                                                   3.85(s, 3H);                                                                   1.40(t, 3H)                            Ij.004                                                                            CHC(Cl)COOCH(CH.sub.3).sub.2                                                Ij.005                                                                            CHC(Br)COOH                                                                 Ij.006                                                                            CHC(Br)COOCH.sub.3                                                          Ij.007                                                                            CHC(Br)COOC.sub.2 H.sub.5                                                   Ij.008                                                                            CHC(Br)COOCH(CH.sub.3).sub.2                                                Ij.009                                                                            CHC(Cl)CONH.sub.2                                                           Ij.010                                                                            CHC(Cl)CONHCH.sub.3                                                         Ij.011                                                                            CHC(Cl)CON(CH.sub.3).sub.2                                                  Ij.012                                                                            CHC(Br)CONH.sub.2                                                           Ij.013                                                                            CHC(Br)CONHCH.sub.3                                                         Ij.014                                                                            CHC(Br)CON(CH.sub.3).sub.2                                                  Ij.015                                                                            CHC(Br)CONH-cyclopropyl                                                     Ij.016                                                                            CHC(Cl)CONH-cyclopropyl                                                     Ij.017                                                                            CH(cyclopropylene)                                                          Ij.018                                                                            CH(cyclopentylene)                                                          Ij.019                                                                            CH(cyclohexylene)                                                           Ij.020                                                                             ##STR148##                                                                 Ij.021                                                                             ##STR149##                                                                 Ij.022                                                                             ##STR150##                                                                 Ij.023                                                                             ##STR151##                                                                 Ij.024                                                                             ##STR152##                                                                 Ij.025                                                                             ##STR153##                                                                 Ij.026                                                                             ##STR154##                                                                 Ij.027                                                                             ##STR155##                                                                 Ij.028                                                                            CHC(CH.sub.3)COOC.sub.2 H.sub.5                                             Ij.029                                                                            CHC(CH.sub.3)COOCH.sub.3                                                    Ij.030                                                                            CHC(CH.sub.3)CONH.sub.2                                                     Ij.031                                                                            CHC(CH.sub.3)CONHCH.sub.3                                                   Ij.032                                                                            CHC(CH.sub.3)CON(CH.sub.3).sub.2                                            Ij.033                                                                            CHC(CN)COOCH.sub.3                                                          Ij.034                                                                            CH.sub.2CH(CN)COOCH.sub.3                                                   Ij.035                                                                            CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                            Ij.036                                                                            CH.sub.2CH(CN)CONH.sub.2                                                    Ij.037                                                                            CH.sub.2CH(CN)CONHCH.sub.3                                                  Ij.038                                                                            CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                           Ij.039                                                                            CH.sub.2CH(CN)CONHSO.sub.2CH.sub.3                                          Ij.040                                                                            CH.sub.2CH(Cl)COOCH.sub.3                                                   Ij.041                                                                            CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                            Ij.042                                                                            CH.sub.2CH(Cl)CONH.sub.2                                                    Ij.043                                                                            CH.sub.2CH(Cl)CONHCH.sub.3                                                  Ij.044                                                                            CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                           Ij.045                                                                            CH.sub.2CH(Cl)CONHSO.sub.2 CH.sub.3                                         Ij.046                                                                            CH.sub.2CH(Br)COOCH.sub.3                                                   Ij.047                                                                            CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                            Ij.048                                                                            CH.sub.2CH(Br)COOCH(CH.sub.3).sub.2                                         Ij.049                                                                            CH.sub.2CH(Br)CONH.sub.2                                                    Ij.050                                                                            CH.sub.2CH(Br)CONHCH.sub.3                                                  Ij.051                                                                            CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                           Ij.052                                                                            CH.sub.2CH(Cl)COCH(CH.sub.3).sub.2                                          Ij.053                                                                            CH.sub.2CH(CN)COCH(CH.sub.3).sub.2                                          Ij.054                                                                            CHCH-(4-fluorophenyl)                                                       Ij.055                                                                            CHCH-(4-chlorophenyl)                                                       Ij.056                                                                            CHCH-(3-trifluoromethylphenyl)                                              Ij.057                                                                            CHCH-(2,4-dichlorophenyl)                                                   Ij.058                                                                            CHC(Cl)COO-cyclohexyl                                                       Ij.059                                                                            CHC(Cl)COOC(CH.sub.3).sub.3                                                 Ij.060                                                                            CHC(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                        Ij.061                                                                            CHC(Cl)CONHCH.sub.2COOCH.sub.3                                              Ij.062                                                                            CHC(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                     Ij.063                                                                            CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                   Ij.064                                                                            CHC(Cl)CONHOC.sub.2 H.sub.5                                                 Ij.065                                                                            CHC(Cl)CONHOCH.sub.3                                                        Ij.066                                                                            CHC(Cl)CONHOCH.sub.2 CHCHCl                                                 Ij.067                                                                            CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                      Ij.068                                                                            CHC(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                        Ij.069                                                                            CHC(Cl)COSCH.sub.2C.sub.2 H.sub.5                                           Ij.070                                                                            CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                        Ij.071                                                                            CHC(COOC.sub.2 H.sub.5).sub.2                                               Ij.072                                                                            CHC(COOCH.sub.3).sub.2                                                      Ij.073                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.3                                              Ij.074                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2 H.sub.5                                      Ij.075                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                       Ij.076                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2phenyl                                        Ij.077                                                                            CHC(Br)COOcyclohexyl                                                        Ij.078                                                                            CHC(Br)COOC(CH.sub.3).sub.3                                                 Ij.079                                                                            CHC(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                        Ij.080                                                                            CHC(Br)CONHCH.sub.2COOCH.sub.3                                              Ij.081                                                                            CHC(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                                     Ij.082                                                                            CHC(Br)CONHOC.sub.2 H.sub.5                                                 Ij.083                                                                            CHC(Br)CONHOCH.sub.3                                                        Ij.084                                                                            CHC(Br)CONHOCH.sub.2CHCHCl                                                  Ij.085                                                                            CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                      Ij.086                                                                            CHC(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                        Ij.087                                                                            CHC(Br)COSCH.sub.2C.sub.2 H.sub.5                                           Ij.088                                                                            CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                        Ij.089                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                    Ij.090                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                        Ij.091                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.3                                              Ij.092                                                                            CHC(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                       Ij.093                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                       Ij.094                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                                      Ij.095                                                                            CH.sub.2CH(Cl)COOcyclohexyl                                                 Ij.096                                                                            CH.sub.2CH(Cl)COOC(CH.sub.3).sub.3                                          Ij.097                                                                            CH.sub.2CH(Cl)COOCH.sub.2CH(CH.sub.3).sub.2                                 Ij.098                                                                            CH.sub.2CH(Cl)CONHCH.sub.2COOCH.sub.3                                       Ij.099                                                                            CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COOCH.sub.3                              Ij.100                                                                            CH.sub.2CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                            Ij.101                                                                            CH.sub.2CH(Cl)CONHOC.sub.2 H.sub.5                                          Ij.102                                                                            CH.sub.2CH(Cl)CONHOCH.sub.3                                                 Ij.103                                                                            CH.sub.2CH(Cl)CONHOCH.sub.2CHCHCl                                           Ij.104                                                                            CH.sub.2CH(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                               Ij.105                                                                            CH.sub.2CH(Cl)COSCH.sub.2COOC.sub.2 H.sub.5                                 Ij.106                                                                            CH.sub.2CH(Cl)COSCH.sub.2C.sub.2 H.sub.5                                    Ij.107                                                                            CH.sub.2CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                                 Ij.108                                                                            CH.sub.2C(Cl)(COOC.sub.2 H.sub.5).sub.2                                     Ij.109                                                                            CH.sub.2C(Cl)(COOCH.sub.3).sub.2                                            Ij.110                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.3                                       Ij.111                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOC.sub.2 H.sub.5                                Ij.112                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                Ij.113                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -phenyl                               Ij.114                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                             Ij.115                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2CHCHCl                                 Ij.116                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                     Ij.117                                                                            CH.sub.2CH(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                  Ij.118                                                                            CH.sub.2CH(Cl)COOH                                                          Ij.119                                                                            CH.sub.2CH(Cl)CONH-cyclopropyl                                              Ij.120                                                                            CH.sub.2CH(Cl)CON(CH.sub.3)CH.sub.2COCO.sub.2 H.sub.5                       Ij.121                                                                            CH.sub.2CH(Cl)CONHCH(CH)CH.sub.3).sub.2)COOC.sub.2 H.sub.5                  Ij.122                                                                            CH.sub.2CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                Ij.123                                                                            CH.sub.2CH(Cl)CO-(2-methoxycarbonyl-pyrrolidin-1-yl)                        Ij.124                                                                            CH.sub.2CH(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.125                                                                            CH.sub.2CH(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                       Ij.126                                                                            CH.sub.2CH(Cl)CON(CN)-cyclopropyl                                           Ij.127                                                                            CH.sub.2CH(Cl)CON(CN)CH.sub.2CHCH.sub.2                                     Ij.128                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5               Ij.129                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)-cyclopropyl                                   Ij.130                                                                            CH.sub.2CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                            Ij.131                                                                            CH.sub.2CH(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                           Ij.132                                                                            CH.sub.2CH(Br)COO-cyclohexyl                                                Ij.133                                                                            CH.sub.2CH(Br)COOC(CH.sub.3).sub.3                                          Ij.134                                                                            CH.sub.2CH(Br)COOCH.sub.2CH(CH.sub.3).sub.2                                 Ij.135                                                                            CH.sub.2CH(Br)CONHCH.sub.2 COOCH.sub.3                                      Ij.136                                                                            CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOCH.sub.3                              Ij.137                                                                            CH.sub.2CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                            Ij.138                                                                            CH.sub.2CH(Br)CONHOC.sub.2 H.sub.5                                          Ij.139                                                                            CH.sub.2CH(Br)CONHOCH.sub.3                                                 Ij.140                                                                            CH.sub.2CH(Br)CONHOCH.sub.2CHCHCl                                           Ij.141                                                                            CH.sub.2CH(Br)CONHCH.sub.2 -(4-chlorophenyl)                                Ij.142                                                                            CH.sub.2CH(Br)COSCH.sub.2COOC.sub.2 H.sub.5                                 Ij.143                                                                            CH.sub.2CH(Br)COSCH.sub.2C.sub.2 H.sub.5                                    Ij.144                                                                            CH.sub.2CH(Br)COSCH.sub.2 -(4-chlorophenyl)                                 Ij.145                                                                            CH.sub.2C(Br)(COOC.sub.2 H.sub.5).sub.2                                     Ij.146                                                                            CH.sub.2C(Br)(COOCH.sub.3).sub.2                                            Ij.147                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.3                                       Ij.148                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOC.sub.2 H.sub.5                                Ij.149                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CH.sub.2C.sub.2 H.sub.5                Ij.150                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -phenyl                               Ij.151                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                             Ij.152                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2CHCHCl                                 Ij.153                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                     Ij.154                                                                            CH.sub.2CH(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                  Ij.155                                                                            CH.sub.2CH(Br)COOH                                                          Ij.156                                                                            CH.sub.2CH(Br)CONH-cyclopropyl                                              Ij.157                                                                            CH.sub.2CH(Br)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                       Ij.158                                                                            CH.sub.2CH(Br)CONHCH(CH(CH.sub.3).sub.2)COOCH.sub.2 H.sub.5                 Ij.159                                                                            CH.sub.2CH(Br)CONHCH(CH.sub.2CH(CH.sub.3).sub.2)COOCH.sub.3                 Ij.160                                                                            CH.sub.2CH(Br)CO-(2-methoxycarbonylpyrrolidin-1-yl)                         Ij.160                                                                            CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.161                                                                            CH.sub.2CH(Br)CONH-(tetrahydrofuran-2-on-3-yl)                              Ij.162                                                                            CH.sub.2CH(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                       Ij.163                                                                            CH.sub.2CH(Br)CON(CN)-cyclopropyl                                           Ij.164                                                                            CH.sub.2CH(Br)CON(CN)CH.sub.2CHCH.sub.2                                     Ij.165                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5               Ij.166                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)-cyclopropyl                                   Ij.167                                                                            CH.sub.2CH(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                             Ij.168                                                                            CH.sub.2CH(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                           Ij.169                                                                            CH.sub.2CH(OH)COOH                                                          Ij.170                                                                            CH.sub.2CH(OH)COOCH.sub.3                                                   Ij.171                                                                            CH.sub.2CH(OH)COOC.sub.2 H.sub.5                                            Ij.172                                                                            CH.sub.2CH(OH)COOCH.sub.2CHNOCH.sub.3                                       Ij.173                                                                            CH.sub.2CH(OH)COOC(CH.sub.3).sub.3                                          Ij.174                                                                            CH.sub.2CH(OH)CONH.sub.2                                                    Ij.175                                                                            CH.sub.2CH(OH)CONHCH.sub.3                                                  Ij.176                                                                            CH.sub.2CH(OH)CONH-cyclopropyl                                              Ij.177                                                                            CH.sub.2CH(OCH.sub.3)COOH                                                   Ij.178                                                                            CH.sub.2CH(OCH.sub.3)COOCH.sub.3                                            Ij.179                                                                            CH.sub.2CH(OCH.sub.3)COOC.sub.2 H.sub.5                                     Ij.180                                                                            CH.sub.2CH(OCH.sub.3)COOCH.sub.2CHNOCH.sub.3                                Ij.181                                                                            CH.sub.2CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                   Ij.182                                                                            CH.sub.2CH(OCH.sub.3)CONH.sub.2                                             Ij.183                                                                            CH.sub.2CH(OCH.sub.3)CONHCH.sub.3                                           Ij.184                                                                            CH.sub.2CH(OCH.sub.3)CONH-cyclopropyl                                       Ij.185                                                                            CH.sub.2CH(OCOCH.sub.3)COOH                                                 Ij.186                                                                            CH.sub.2CH(OCOCH.sub.3)COOCH.sub.3                                          Ij.187                                                                            CH.sub.2CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                   Ij.188                                                                            CH.sub.2CH(OCOCH.sub.3)COOCH.sub.2CHNOCH.sub.3                              Ij.189                                                                            CH.sub.2CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                                 Ij.190                                                                            CH.sub.2CH(OCOCH.sub.3)CONH.sub.2                                           Ij.191                                                                            CH.sub.2CH(OCOCH.sub.3)CONHCH.sub.3                                         Ij.192                                                                            CH.sub.2CH(OCOCH.sub.3)CONH-cyclopropyl                                     Ij.193                                                                            CH.sub.2CH(NH.sub.2)COOH                                                    Ij.194                                                                            CH.sub.2CH(NH.sub.2)COOCH.sub.3                                             Ij.195                                                                            CH.sub.2CH(NH.sub.2)COOC.sub.2 H.sub.5                                      Ij.196                                                                            CH.sub.2CH(NH.sub.2)COOC(CH.sub.3).sub.3                                    Ij.197                                                                            CH.sub.2CH(NH.sub.2)CONH.sub.2                                              Ij.198                                                                            CH.sub.2CH(NH.sub.2)CONHCH.sub.3                                            Ij.199                                                                            CH.sub.2CH(N.sub.3)COOH                                                     Ij.200                                                                            CH.sub.2CH(N.sub.3)COOCH.sub.3                                              Ij.201                                                                            CH.sub.2CH(N.sub.3)COOC.sub.2 H.sub.5                                       Ij.202                                                                            CH.sub.2CH(N.sub.3)COOC(CH.sub.3).sub.3                                     Ij.203                                                                            CH.sub.2CH(N.sub.3)CONH.sub.2                                               Ij.204                                                                            CH.sub.2CH(N.sub.3)CONHCH.sub.3                                             Ij.205                                                                            CH.sub.2CH(NHCOCH.sub.3)COOH                                                Ij.206                                                                            CH.sub.2CH(NHCOCH.sub.3)COOCH.sub.3                                         Ij.207                                                                            CH.sub.2CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                  Ij.208                                                                            CH.sub.2CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                                Ij.209                                                                            CH.sub.2CH(NHCOCH.sub.3)CONH.sub.2                                          Ij.210                                                                            CH.sub.2CH(NHCOCH.sub.3)CONHCH.sub.3                                        Ij.211                                                                            CH.sub.2CH.sub.2cyclohexyl                                                  Ij.212                                                                            CH.sub.2CH.sub.2cyclopentyl                                                 Ij.213                                                                            CH.sub.2CH.sub.2cyclopropyl                                                 Ij.214                                                                            CH.sub.2CH.sub.2phenyl                                                      Ij.215                                                                            CHC(CN)COOC.sub.2 H.sub.5                                                   Ij.216                                                                            CHC(CN)COOCH(CH.sub.3).sub.2                                                Ij.217                                                                            CHC(CN)COOC(CH.sub.3).sub.3                                                 Ij.218                                                                            CHC(CN)COOCH.sub.2CHNOCH.sub.2CHCH.sub.2                                    Ij.219                                                                            CHC(CN)COOCH.sub.2CHNOCH.sub.2CHCHCl                                        Ij.220                                                                            CHC(Cl)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                            Ij.221                                                                            CHC(Cl)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                         Ij.222                                                                            CHC(Cl)COO-(4-acetoxytetrahydrofuran-3-yl)                                  Ij.223                                                                            CHC(Cl)CONH-cyclohexyl                                                      Ij.224                                                                            CHC(Cl)CON(CH.sub.3)CH.sub.2COOC.sub.2 H.sub.5                              Ij.225                                                                            CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                         Ij.226                                                                            CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                       Ij.227                                                                            CHC(Cl)CO-(2-methoxycarbonylpyrrolidin-1-yl)                                Ij.228                                                                            CHC(Cl)CONH-(tetrahydrofuran-2-on-3-yl)                                     Ij.229                                                                            CHC(Cl)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                              Ij.230                                                                            CHC(Cl)CON(CN)-cyclopropyl                                                  Ij.231                                                                            CHC(Cl)CON(CN)CH.sub.2CHCH.sub.2                                            Ij.232                                                                            CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ij.233                                                                            CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                          Ij.234                                                                            CHC(Cl)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                    Ij.235                                                                            CHC(Br)COOCH.sub.2CHNOCH.sub.2 -(4-chlorophenyl)                            Ij.236                                                                            CHC(Br)COOCH.sub.2CHNOCH(CH.sub.3)-(4-chlorophenyl)                         Ij.237                                                                            CHC(Br)COO-(4-acetoxytetrahydrofuran-3-yl)                                  Ij.238                                                                            CHC(Br)CONH-cyclohexyl                                                      Ij.239                                                                            CHC(Br)CON(CH.sub.3)CH.sub.2COCO.sub.2 H.sub.5                              Ij.240                                                                            CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                         Ij.241                                                                            CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)COOCH.sub.3                       Ij.242                                                                            CHC(Br)CO-(2-methoxycarbonylpyrrolidin-1-yl)                                Ij.243                                                                            CHC(Br)CONH-(tetrahydrofuran-2-on-3-yl)                                     Ij.244                                                                            CHC(Br)CON(CN)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                              Ij.245                                                                            CHC(Br)CON(CN)-cyclopropyl                                                  Ij.246                                                                            CHC(Br)CON(CN)CH.sub.2CHCH.sub.2                                            Ij.247                                                                            CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2C.sub.2 H.sub.5                      Ij.248                                                                            CHC(Br)CON(CONH.sub.2)-cyclopropyl                                          Ij.249                                                                            CHC(Br)CON(CONH.sub.2)CH.sub.2CHCH.sub.2                                    Ij.250                                                                            CH.sub.2CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                    Ij.251                                                                            CH.sub.2CH(Br)CON(C.sub.2 H.sub.5).sub.2                                    Ij.252                                                                            CHCH(Br)CON(C.sub.2 H.sub.5).sub.2                                          Ij.253                                                                            CHCH(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Ij.254                                                                             ##STR156##                                                                 Ij.255                                                                             ##STR157##                                                                 Ij.256                                                                             ##STR158##                                                                 Ij.257                                                                             ##STR159##                                                                 Ij.258                                                                             ##STR160##                                                                 Ij.259                                                                             ##STR161##                                                                 Ij.260                                                                             ##STR162##                                                                 Ij.261                                                                             ##STR163##                                                                 Ij.262                                                                             ##STR164##                                                                 __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________      ##STR165##                                                                                                     m.p./.sup.1 H-NMR  ppm!                       No. R.sup.1                      MS  mz.sup.-1 !                               __________________________________________________________________________     Im.001                                                                             CHC(Cl)COOH                                                                Im.002                                                                             CHC(Cl)COOCH.sub.3                                                         Im.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Im.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Im.005                                                                             CHC(Br)COOH                                                                Im.006                                                                             CHC(Br)COOCH.sub.3                                                         Im.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Im.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Im.009                                                                             CHC(Cl)CONH.sub.2                                                          Im.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Im.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Im.012                                                                             CHC(Br)CONH.sub.2                                                          Im.013                                                                             CHC(Br)CONHCH.sub.3                                                        Im.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Im.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Im.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Im.017                                                                             CH(cyclopropylene)                                                         Im.018                                                                             CH(cyclopentylene)                                                         Im.019                                                                             CH(cyclohexylene)                                                          Im.020                                                                              ##STR166##                                                                Im.021                                                                              ##STR167##                                                                Im.022                                                                              ##STR168##                                                                Im.023                                                                              ##STR169##                                                                Im.024                                                                              ##STR170##                                                                Im.025                                                                              ##STR171##                                                                Im.026                                                                              ##STR172##                                                                Im.027                                                                              ##STR173##                                                                Im.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Im.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Im.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Im.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Im.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Im.033                                                                             CHC(CN)COOCH.sub.3                                                         Im.034                                                                             CH.sub.2 CH(CN)COOCH.sub.3                                                 Im.035                                                                             CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                          Im.036                                                                             CH.sub.2 CH(CN)CONH.sub.2                                                  Im.037                                                                             CH.sub.2 CH(CN)CONHCH.sub.3                                                Im.038                                                                             CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                         Im.039                                                                             CH.sub.2 CH(CN)CONHSO.sub.2 CH.sub.3                                       Im.040                                                                             CH.sub.2 CH(Cl)COOCH.sub.3                                                 Im.041                                                                             CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                          Im.042                                                                             CH.sub.2 CH(Cl)CONH.sub.2                                                  Im.043                                                                             CH.sub.2 CH(Cl)CONHCH.sub.3                                                Im.044                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                         Im.045                                                                             CH.sub.2 CH(Cl)CONHSO.sub.2 CH.sub.3                                       Im.046                                                                             CH.sub.2 CH(Br)COOCH.sub.3                                                 Im.047                                                                             CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                          Im.048                                                                             CH.sub.2 CH(Br)COOCH(CH.sub.3).sub.2                                       Im.049                                                                             CH.sub.2 CH(Br)CONH.sub.2                                                  Im.050                                                                             CH.sub.2 CH(Br)CONHCH.sub.3                                                Im.051                                                                             CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                         Im.052                                                                             CH.sub.2 CH(Cl)COCH(CH.sub.3).sub.2                                        Im.053                                                                             CH.sub.2 CH(CN)COCH(CH.sub.3).sub.2                                        Im.054                                                                             CHCH-(4-fluorophenyl)                                                      Im.055                                                                             CHCH-(4-chlorophenyl)                                                      Im.056                                                                             CHCH-(3-trifluoromethylphenyl)                                             Im.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Im.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Im.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Im.060                                                                             CHC(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Im.061                                                                             CHC(Cl)CONHCH.sub.2 COOCH.sub.3                                            Im.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Im.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Im.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Im.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Im.066                                                                             CHC(Cl)CONHOCH.sub.2 CHCHCl                                                Im.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Im.068                                                                             CHC(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Im.069                                                                             CHC(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                         Im.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Im.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Im.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Im.073                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.3                                            Im.074                                                                             CHC(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Im.075                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Im.076                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Im.077                                                                             CHC(Br)COO-cyclohexyl                                                      Im.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Im.079                                                                             CHC(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Im.080                                                                             CHC(Br)CONHCH.sub.2 COOCH.sub.3                                            Im.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Im.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Im.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Im.084                                                                             CHC(Br)CONHOCH.sub.2 CHCHCl                                                Im.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Im.086                                                                             CHC(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Im.087                                                                             CHC(Br)COSCH.sub.2 C.sub.2 H.sub.5                                         Im.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Im.089                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Im.090                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Im.091                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.3                                            Im.092                                                                             CHC(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Im.093                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Im.094                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Im.095                                                                             CH.sub.2 CH(Cl)COO-cyclohexyl                                              Im.096                                                                             CH.sub.2 CH(Cl)COOC(CH.sub.3).sub.3                                        Im.097                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                              Im.098                                                                             CH.sub.2 CH(Cl)CONHCH.sub.2 COOCH.sub.3                                    Im.099                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Im.100                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Im.101                                                                             CH.sub.2 CH(Cl)CONHOC.sub.2 H.sub.5                                        Im.102                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.3                                               Im.103                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 CHCHCl                                        Im.104                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 -                                                 (4-chlorophenyl)                                                           Im.105                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                              Im.106                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                 Im.107                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 -(4-chlorophenyl)                               Im.108                                                                             CH.sub.2 C(Cl)(COOC.sub.2 H.sub.5).sub.2                                   Im.109                                                                             CH.sub.2 C(Cl)(COOCH.sub.3).sub.2                                          Im.110                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.3                                    Im.111                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Im.112                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Im.113                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Im.114                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Im.115                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Im.116                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 -                                      (4-chlorophenyl)                                                           Im.117                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Im.118                                                                             CH.sub.2 CH(Cl)COOH                                                        Im.119                                                                             CH.sub.2 CH(Cl)CONH-cyclopropyl                                            Im.120                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Im.121                                                                             CH.sub.2 CH(Cl)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Im.122                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Im.123                                                                             CH.sub.2 CH(Cl)CO-(2-methoxycarbonyl-                                          pyrrolidin-1-yl)                                                           Im.124                                                                             CH.sub.2 CH(Cl)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Im.125                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Im.126                                                                             CH.sub.2 CH(Cl)CON(CN)-cyclopropyl                                         Im.127                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                  Im.128                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Im.129                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)-cyclopropyl                                 Im.130                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Im.131                                                                             CH.sub.2 CH(Cl)COO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Im.132                                                                             CH.sub.2 CH(Br)COO-cyclohexyl                                              Im.133                                                                             CH.sub.2 CH(Br)COOC(CH.sub.3).sub.3                                        Im.134                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                              Im.135                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 COOCH.sub.3                                    Im.136                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Im.137                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Im.138                                                                             CH.sub.2 CH(Br)CONHOC.sub.2 H.sub.5                                        Im.139                                                                             CH.sub.2 CH(Br)CONHOCH.sub.3                                               Im.140                                                                             CH.sub.2 CH(Br)CONHOCH.sub.2 CHCHCl                                        Im.141                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 -                                                  (4-chlorophenyl)                                                           Im.142                                                                             CH.sub.2 CH(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                              Im.143                                                                             CH.sub.2 CH(Br)COSCH.sub.2 C.sub.2 H.sub.5                                 Im.144                                                                             CH.sub.2 CH(Br)COSCH.sub.2 -(4-chlorophenyl)                               Im.145                                                                             CH.sub.2 C(Br)(COOC.sub.2 H.sub.5).sub.2                                   Im.146                                                                             CH.sub.2 C(Br)(COOCH.sub.3).sub.2                                          Im.147                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.3                                    Im.148                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Im.149                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Im.150                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Im.151                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Im.152                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Im.153                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Im.154                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Im.155                                                                             CH.sub.2 CH(Br)COOH                                                        Im.156                                                                             CH.sub.2 CH(Br)CONH-cyclopropyl                                            Im.157                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Im.158                                                                             CH.sub.2 CH(Br)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Im.159                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Im.160                                                                             CH.sub.2 CH(Br)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Im.161                                                                             CH.sub.2 CH(Br)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Im.162                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Im.163                                                                             CH.sub.2 CH(Br)CON(CN)-cyclopropyl                                         Im.164                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CHCH.sub.2                                  Im.165                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Im.166                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)-cyclopropyl                                 Im.167                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Im.168                                                                             CH.sub.2 CH(BryCOO-(4-acetoxytetra-                                            hydrofuran-3-yl)                                                           Im.169                                                                             CH.sub.2 CH(OH)COOH                                                        Im.170                                                                             CH.sub.2 CH(OH)COOCH.sub.3                                                 Im.171                                                                             CH.sub.2 CH(OH)COOC.sub.2 H.sub.5                                          Im.172                                                                             CH.sub.2 CH(OH)COOCH.sub.2 CHNOCH.sub.3                                    Im.173                                                                             CH.sub.2 CH(OH)COOC(CH.sub.3).sub.3                                        Im.174                                                                             CH.sub.2 CH(OH)CONH.sub.2                                                  Im.175                                                                             CH.sub.2 CH(OH)CONHCH.sub.3                                                Im.176                                                                             CH.sub.2 CH(OH)CONH-cyclopropyl                                            Im.177                                                                             CH.sub.2 CH(OCH.sub.3)COOH                                                 Im.178                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                          Im.179                                                                             CH.sub.2 CH(OCH.sub.3)COOC.sub.2 H.sub.5                                   Im.180                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                             Im.181                                                                             CH.sub.2 CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                 Im.182                                                                             CH.sub.2 CH(OCH.sub.3)CONH.sub.2                                           Im.183                                                                             CH.sub.2 CH(OCH.sub.3)CONHCH.sub.3                                         Im.184                                                                             CH.sub.2 CH(OCH.sub.3)CONH-cyclopropyl                                     Im.185                                                                             CH.sub.2 CH(OCOCH.sub.3)COOH                                               Im.186                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.3                                        Im.187                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                 Im.188                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                           Im.189                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                               Im.190                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH.sub.2                                         Im.191                                                                             CH.sub.2 CH(OCOCH.sub.3)CONHCH.sub.3                                       Im.192                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH-cyclopropyl                                   Im.193                                                                             CH.sub.2 CH(NH.sub.2)COOH                                                  Im.194                                                                             CH.sub.2 CH(NH.sub.2)COOCH.sub.3                                           Im.195                                                                             CH.sub.2 CH(NH.sub.2)COOC.sub.2 H.sub.5                                    Im.196                                                                             CH.sub.2 CH(NH.sub.2)COOC(CH.sub.3).sub.3                                  Im.197                                                                             CH.sub.2 CH(NH.sub.2)CONH.sub.2                                            Im.198                                                                             CH.sub.2 CH(NH.sub.2)CONHCH.sub.3                                          Im.199                                                                             CH.sub.2 CH(N.sub.3)COOH                                                   Im.200                                                                             CH.sub.2 CH(N.sub.3)COOCH.sub.3                                            Im.201                                                                             CH.sub.2 CH(N.sub.3)COOC.sub.2 H.sub.5                                     Im.202                                                                             CH.sub.2 CH(N.sub.3)COOC(CH.sub.3).sub.3                                   Im.203                                                                             CH.sub.2 CH(N.sub.3)CONH.sub.2                                             Im.204                                                                             CH.sub.2 CH(N.sub.3)CONHCH.sub.3                                           Im.205                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOH                                              Im.206                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOCH.sub.3                                       Im.207                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                Im.208                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                              Im.209                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONH.sub.2                                        Im.210                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONHCH.sub.3                                      Im.211                                                                             CH.sub.2 CH.sub.2 -cyclohexyl                                              Im.212                                                                             CH.sub.2 CH.sub.2 -cyclopentyl                                             Im.213                                                                             CH.sub.2 CH.sub.2 -cyclopropyl                                             Im.214                                                                             CH.sub.2 CH.sub.2 -phenyl                                                  Im.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Im.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Im.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Im.218                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Im.219                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Im.220                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Im.221                                                                             CHC(Cl)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Im.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Im.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Im.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Im.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Im.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Im.227                                                                             CHC(Cl)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Im.228                                                                             CHC(Cl)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Im.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Im.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Im.231                                                                             CHC(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                          Im.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Im.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Im.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Im.235                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -                                              (4-chlorophenyl)                                                           Im.236                                                                             CHC(Br)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Im.237                                                                             CHC(Br)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Im.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Im.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Im.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Im.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Im.242                                                                             CHC(Br)CO-(2-methoxycarbonyl-                                                  pyrrolidin-1-yl)                                                           Im.243                                                                             CHC(Br)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Im.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Im.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Im.246                                                                             CHC(Br)CON(CN)CH.sub.2 CHCH.sub.2                                          Im.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Im.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Im.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Im.250                                                                             CH.sub.2 CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                  Im.251                                                                             CH.sub.2 CH(Br)CON(C.sub.2 H.sub.5).sub.2                                  Im.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Im.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Im.254                                                                              ##STR174##                                                                Im.255                                                                              ##STR175##                                                                Im.256                                                                              ##STR176##                                                                Im.257                                                                              ##STR177##                                                                Im.258                                                                              ##STR178##                                                                Im.259                                                                              ##STR179##                                                                Im.260                                                                              ##STR180##                                                                Im.261                                                                              ##STR181##                                                                Im.262                                                                              ##STR182##                                                                __________________________________________________________________________

                  TABLE 14                                                         ______________________________________                                          ##STR183##                                                                                               m.p./.sup.1 H-NMR  ppm!                             No.   R.sup.1              MS  mz.sup.-1 !                                     ______________________________________                                         In.001                                                                               CHC(Cl)COOH                                                              In.002                                                                               CHC(Cl)COOCH.sub.3                                                       In.003                                                                               CHC(Cl)COOC.sub.2 H.sub.5                                                In.004                                                                               CHC(Cl)COOCH(CH.sub.3).sub.2                                             In.005                                                                               CHC(Br)COOH                                                              In.006                                                                               CHC(Br)COOCH.sub.3                                                       In.007                                                                               CHC(Br)COOC.sub.2 H.sub.5                                                In.008                                                                               CHC(Br)COOCH(CH.sub.3).sub.2                                             In.009                                                                               CHC(Cl)CONH.sub.2                                                        In.010                                                                               CHC(Cl)CONHCH.sub.3                                                      In.011                                                                               CHC(Cl)CON(CH.sub.3).sub.2                                               In.012                                                                               CHC(Br)CONH.sub.2                                                        In.013                                                                               CHC(Br)CONHCH.sub.3                                                      In.014                                                                               CHC(Br)CON(CH.sub.3).sub.2                                               In.015                                                                               CHC(Br)CONH-cyclopropyl                                                  In.016                                                                               CHC(Cl)CONH-cyclopropyl                                                  In.017                                                                               CH(cyclopropylene)                                                       In.018                                                                               CH(cyclopentylene)                                                       In.019                                                                               CH(cyclohexylene)                                                        In.020                                                                                ##STR184##                                                              In.021                                                                                ##STR185##                                                              In.022                                                                                ##STR186##                                                              In.023                                                                                ##STR187##                                                              In.024                                                                                ##STR188##                                                              In.025                                                                                ##STR189##                                                              In.026                                                                                ##STR190##                                                              In.027                                                                                ##STR191##                                                              In.028                                                                               CHC(CH.sub.3)COOC.sub.2 H.sub.5                                          In.029                                                                               CHC(CH.sub.3)COOCH.sub.3                                                 In.030                                                                               CHC(CH.sub.3)CONH.sub.2                                                  In.031                                                                               CHC(CH.sub.3)CONHCH.sub.3                                                In.032                                                                               CHC(CH.sub.3)CON(CH.sub.3).sub.2                                         In.033                                                                               CHC(CN)COOCH.sub.3                                                       In.034                                                                               CH.sub.2 CH(CN)COOCH.sub.3                                               In.035                                                                               CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                        In.036                                                                               CH.sub.2 CH(CN)CONH.sub.2                                                In.037                                                                               CH.sub.2 CH(CN)CONHCH.sub.3                                              In.038                                                                               CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                       In.039                                                                               CH.sub.2 CH(CN)CONHSO.sub.2 CH.sub.3                                     In.040                                                                               CH.sub.2 CH(Cl)COOCH.sub.3                                               In.041                                                                               CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                        In.042                                                                               CH.sub.2 CH(Cl)CONH.sub.2                                                In.043                                                                               CH.sub.2 CH(Cl)CONHCH.sub.3                                              In.044                                                                               CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                       In.045                                                                               CH.sub.2 CH(Cl)CONHSO.sub.2 CH.sub.3                                     In.046                                                                               CH.sub.2 CH(Br)COOCH.sub.3                                               In.047                                                                               CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                        In.048                                                                               CH.sub.2 CH(Br)COOCH(CH.sub.3).sub.2                                     In.049                                                                               CH.sub.2 CH(Br)CONH.sub.2                                                In.050                                                                               CH.sub.2 CH(Br)CONHCH.sub.3                                              In.051                                                                               CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                       In.052                                                                               CH.sub.2 CH(Cl)COCH(CH.sub.3).sub.2                                      In.053                                                                               CH.sub.2 CH(CN)COCH(CH.sub.3).sub.2                                      In.054                                                                               CHCH-(4-fluorophenyl)                                                    In.055                                                                               CHCH-(4-chlorophenyl)                                                    In.056                                                                               CHCH-(3-trifluoromethylphenyl)                                           In.057                                                                               CHCH-(2,4-dichlorophenyl)                                                ______________________________________                                    

                                      TABLE 15                                     __________________________________________________________________________      ##STR192##                                                                                                     m.p./.sup.1 H-NMR  ppm!                       No. R.sup.1                      MS  mz.sup.-1 !                               __________________________________________________________________________     Io.001                                                                             CHC(Cl)COOH                                                                Io.002                                                                             CHC(Cl)COOCH.sub.3                                                         Io.003                                                                             CHC(Cl)COOC.sub.2 H.sub.5                                                  Io.004                                                                             CHC(Cl)COOCH(CH.sub.3).sub.2                                               Io.005                                                                             CHC(Br)COOH                                                                Io.006                                                                             CHC(Br)COOCH.sub.3                                                         Io.007                                                                             CHC(Br)COOC.sub.2 H.sub.5                                                  Io.008                                                                             CHC(Br)COOCH(CH.sub.3).sub.2                                               Io.009                                                                             CHC(Cl)CONH.sub.2                                                          Io.010                                                                             CHC(Cl)CONHCH.sub.3                                                        Io.011                                                                             CHC(Cl)CON(CH.sub.3).sub.2                                                 Io.012                                                                             CHC(Br)CONH.sub.2                                                          Io.013                                                                             CHC(Br)CONHCH.sub.3                                                        Io.014                                                                             CHC(Br)CON(CH.sub.3).sub.2                                                 Io.015                                                                             CHC(Br)CONH-cyclopropyl                                                    Io.016                                                                             CHC(Cl)CONH-cyclopropyl                                                    Io.017                                                                             CH(cyclopropylene)                                                         Io.018                                                                             CH(cyclopentylene)                                                         Io.019                                                                             CH(cyclohexylene)                                                          Io.020                                                                              ##STR193##                                                                Io.021                                                                              ##STR194##                                                                Io.022                                                                              ##STR195##                                                                Io.023                                                                              ##STR196##                                                                Io.024                                                                              ##STR197##                                                                Io.025                                                                              ##STR198##                                                                Io.026                                                                              ##STR199##                                                                Io.027                                                                              ##STR200##                                                                Io.028                                                                             CHC(CH.sub.3)COOC.sub.2 H.sub.5                                            Io.029                                                                             CHC(CH.sub.3)COOCH.sub.3                                                   Io.030                                                                             CHC(CH.sub.3)CONH.sub.2                                                    Io.031                                                                             CHC(CH.sub.3)CONHCH.sub.3                                                  Io.032                                                                             CHC(CH.sub.3)CON(CH.sub.3).sub.2                                           Io.033                                                                             CHC(CN)COOCH.sub.3                                                         Io.034                                                                             CH.sub.2 CH(CN)COOCH.sub.3                                                 Io.035                                                                             CH.sub.2 CH(CN)COOC.sub.2 H.sub.5                                          Io.036                                                                             CH.sub.2 CH(CN)CONH.sub.2                                                  Io.037                                                                             CH.sub.2 CH(CN)CONHCH.sub.3                                                Io.038                                                                             CH.sub.2 CH(CN)CON(CH.sub.3).sub.2                                         Io.039                                                                             CH.sub.2 CH(CN)CONHSO.sub.2 CH.sub.3                                       Io.040                                                                             CH.sub.2 CH(Cl)COOCH.sub.3                                                 Io.041                                                                             CH.sub.2 CH(Cl)COOC.sub.2 H.sub.5                                          Io.042                                                                             CH.sub.2 CH(Cl)CONH.sub.2                                                  Io.043                                                                             CH.sub.2 CH(Cl)CONHCH.sub.3                                                Io.044                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3).sub.2                                         Io.045                                                                             CH.sub.2 CH(Cl)CONHSO.sub.2 CH.sub.3                                       Io.046                                                                             CH.sub.2 CH(Br)COOCH.sub.3                                                 Io.047                                                                             CH.sub.2 CH(Br)COOC.sub.2 H.sub.5                                          Io.048                                                                             CH.sub.2 CH(Br)COOCH(CH.sub.3).sub.2                                       Io.049                                                                             CH.sub.2 CH(Br)CONH.sub.2                                                  Io.050                                                                             CH.sub.2 CH(Br)CONHCH.sub.3                                                Io.051                                                                             CH.sub.2 CH(Br)CON(CH.sub.3).sub.2                                         Io.052                                                                             CH.sub.2 CH(Cl)COCH(CH.sub.3).sub.2                                        Io.053                                                                             CH.sub.2 CH(CN)COCH(CH.sub.3).sub.2                                        Io.054                                                                             CHCH-(4-fluorophenyl)                                                      Io.055                                                                             CHCH-(4-chlorophenyl)                                                      Io.056                                                                             CHCH-(3-trifluoromethylphenyl)                                             Io.057                                                                             CHCH-(2,4-dichlorophenyl)                                                  Io.058                                                                             CHC(Cl)COO-cyclohexyl                                                      Io.059                                                                             CHC(Cl)COOC(CH.sub.3).sub.3                                                Io.060                                                                             CHC(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Io.061                                                                             CHC(Cl)CONHCH.sub.2 COOCH.sub.3                                            Io.062                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Io.063                                                                             CHC(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                                  Io.064                                                                             CHC(Cl)CONHOC.sub.2 H.sub.5                                                Io.065                                                                             CHC(Cl)CONHOCH.sub.3                                                       Io.066                                                                             CHC(Cl)CONHOCH.sub.2 CHCHCl                                                Io.067                                                                             CHC(Cl)CONHOCH.sub.2 -(4-chlorophenyl)                                     Io.068                                                                             CHC(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Io.069                                                                             CHC(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                         Io.070                                                                             CHC(Cl)COSCH.sub.2 -(4-chlorophenyl)                                       Io.071                                                                             CHC(COOC.sub.2 H.sub.5).sub.2                                              Io.072                                                                             CHC(COOCH.sub.3).sub.2                                                     Io.073                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.3                                            Io.074                                                                             CHC(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Io.075                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Io.076                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Io.077                                                                             CHC(Br)COO-cyclohexyl                                                      Io.078                                                                             CHC(Br)COOC(CH.sub.3).sub.3                                                Io.079                                                                             CHC(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                                      Io.080                                                                             CHC(Br)CONHCH.sub.2 COOCH.sub.3                                            Io.081                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                                   Io.082                                                                             CHC(Br)CONHOC.sub.2 H.sub.5                                                Io.083                                                                             CHC(Br)CONHOCH.sub.3                                                       Io.084                                                                             CHC(Br)CONHOCH.sub.2 CHCHCl                                                Io.085                                                                             CHC(Br)CONHOCH.sub.2 -(4-chlorophenyl)                                     Io.086                                                                             CHC(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                                      Io.087                                                                             CHC(Br)COSCH.sub.2 C.sub.2 H.sub.5                                         Io.088                                                                             CHC(Br)COSCH.sub.2 -(4-chlorophenyl)                                       Io.089                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Io.090                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Io.091                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.3                                            Io.092                                                                             CHC(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                                     Io.093                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5                   Io.094                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                                    Io.095                                                                             CH.sub.2 CH(Cl)COO-cyclohexyl                                              Io.096                                                                             CH.sub.2 CH(Cl)COOC(CH.sub.3).sub.3                                        Io.097                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CH(CH.sub.3).sub.2                              Io.098                                                                             CH.sub.2 CH(Cl)CONHCH.sub.2 COOCH.sub.3                                    Io.099                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Io.100                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Io.101                                                                             CH.sub.2 CH(Cl)CONHOC.sub.2 H.sub.5                                        Io.102                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.3                                               Io.103                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 CHCHCl                                        Io.104                                                                             CH.sub.2 CH(Cl)CONHOCH.sub.2 -                                                 (4-chlorophenyl)                                                           Io.105                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 COOC.sub.2 H.sub.5                              Io.106                                                                             CH.sub.2 CH(Cl)COSCH.sub.2 C.sub.2 H.sub.5                                 Io.107                                                                             CH.sub.2 CH(Cl)CO-SCH.sub.2 -(4-chlorophenyl)                              Io.108                                                                             CH.sub.2 C(Cl)(COOC.sub.2 H.sub.5).sub.2                                   Io.109                                                                             CH.sub.2 C(Cl)(COOCH.sub.3).sub.2                                          Io.110                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.3                                    Io.111                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Io.112                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Io.113                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Io.114                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Io.115                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Io.116                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Io.117                                                                             CH.sub.2 CH(Cl)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Io.118                                                                             CH.sub.2 CH(Cl)COOH                                                        Io.119                                                                             CH.sub.2 CH(Cl)CONH-cyclopropyl                                            Io.120                                                                             CH.sub.2 CH(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Io.121                                                                             CH.sub.2 CH(Cl)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Io.122                                                                             CH.sub.2 CH(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Io.123                                                                             CH.sub.2 CH(Cl)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Io.124                                                                             CH.sub.2 CH(Cl)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Io.125                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Io.126                                                                             CH.sub.2 CH(Cl)CON(CN)-cyclopropyl                                         Io.127                                                                             CH.sub.2 CH(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                  Io.128                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Io.129                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)-cyclopropyl                                 Io.130                                                                             CH.sub.2 CH(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Io.131                                                                             CH.sub.2 CH(Cl)COO-(4-acetoxytetrahy-                                          drofuran-3-yl)                                                             Io.132                                                                             CH.sub.2 CH(Br)COO-cyclohexyl                                              Io.133                                                                             CH.sub.2 CH(Br)COOC(CH.sub.3).sub.3                                        Io.134                                                                             CHzCH(Br)COOCH.sub.2 CH(CH.sub.3).sub.2                                    Io.135                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 COOCH.sub.3                                    Io.136                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOCH.sub.3                           Io.137                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.3)COOC.sub.2 H.sub.5                          Io.138                                                                             CH.sub.2 CH(Br)CONHOC.sub.2 H.sub.5                                        Io.139                                                                             CH.sub.2 CH(Br)CONHOCH.sub.3                                               Io.140                                                                             CH.sub.2 CH(Br)CONHOCH.sub.2 CHCHCl                                        Io.141                                                                             CH.sub.2 CH(Br)CONHCH.sub.2 -                                                  (4-chlorophenyl)                                                           Io.142                                                                             CH.sub.2 CH(Br)COSCH.sub.2 COOC.sub.2 H.sub.5                              Io.143                                                                             CH.sub.2 CH(Br)COSCH.sub.2 C.sub.2 H.sub.5                                 Io.144                                                                             CH.sub.2 CH(Br)COSCH.sub.2 -(4-chlorophenyl)                               Io.145                                                                             CH.sub.2 C(Br)(COOC.sub.2 H.sub.5).sub.2                                   Io.146                                                                             CH.sub.2 C(Br)(COOCH.sub.3).sub.2                                          Io.147                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.3                                    Io.148                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOC.sub.2 H.sub.5                             Io.149                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CH.sub.2 C.sub.2 H.sub.5           Io.150                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 -phenyl                            Io.151                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                         Io.152                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                             Io.153                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH.sub.2 -(4-chlorophenyl)                                                Io.154                                                                             CH.sub.2 CH(Br)COOCH.sub.2 CHN                                                 OCH(CH.sub.3)-(4-chlorophenyl)                                             Io.155                                                                             CH.sub.2 CH(Br)COOH                                                        Io.156                                                                             CH.sub.2 CH(Br)CONH-cyclopropyl                                            Io.157                                                                             CH.sub.2 CH(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                    Io.158                                                                             CH.sub.2 CH(Br)CO                                                              NHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                                 Io.159                                                                             CH.sub.2 CH(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                           OCH.sub.3                                                                  Io.160                                                                             CH.sub.2 CH(Br)CO(2-methoxycarbonyl-                                           pyrrolidin-1-yl)                                                           Io.161                                                                             CH.sub.2 CH(Br)CONH-(tetrahydro-                                               furan-2-on-3-yl)                                                           Io.162                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Io.163                                                                             CH.sub.2 CH(Br)CON(CN)-cyclopropyl                                         Io.164                                                                             CH.sub.2 CH(Br)CON(CN)CH.sub.2 CHCH.sub.2                                  Io.165                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5            Io.166                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)-cyclopropyl                                 Io.167                                                                             CH.sub.2 CH(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                          Io.168                                                                             CH.sub.2 CH(Br)COO-(4-acetoxytetrahy-                                          drofuran-3-yl)                                                             Io.169                                                                             CH.sub.2 CH(OH)COOH                                                        Io.170                                                                             CH.sub.2 CH(OH)COOCH.sub.3                                                 Io.171                                                                             CH.sub.2 CH(OH)COOC.sub.2 H.sub.5                                          Io.172                                                                             CH.sub.2 CH(OH)COOCH.sub.2 CHNOCH.sub.3                                    Io.173                                                                             CH.sub.2 CH(OH)COOC(CH.sub.3).sub.3                                        Io.174                                                                             CH.sub.2 CH(OH)CONH.sub.2                                                  Io.175                                                                             CH.sub.2 CH(OH)CONHCH.sub.3                                                Io.176                                                                             CH.sub.2 CH(OH)CONH-cyclopropyl                                            Io.177                                                                             CH.sub.2 CH(OCH.sub.3)COOH                                                 Io.178                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.3                                          Io.179                                                                             CH.sub.2 CH(OCH.sub.3)COOC.sub.2 H.sub.5                                   Io.180                                                                             CH.sub.2 CH(OCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                             Io.181                                                                             CH.sub.2 CH(OCH.sub.3)COOC(CH.sub.3).sub.3                                 Io.182                                                                             CH.sub.2 CH(OCH.sub.3)CONH.sub.2                                           Io.183                                                                             CH.sub.2 CH(OCH.sub.3)CONHCH.sub.3                                         Io.184                                                                             CH.sub.2 CH(OCH.sub.3)CONH-cyclopropyl                                     Io.185                                                                             CH.sub.2 CH(OCOCH.sub.3)COOH                                               Io.186                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.3                                        Io.187                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC.sub.2 H.sub.5                                 Io.188                                                                             CH.sub.2 CH(OCOCH.sub.3)COOCH.sub.2 CHNOCH.sub.3                           Io.189                                                                             CH.sub.2 CH(OCOCH.sub.3)COOC(CH.sub.3).sub.3                               Io.190                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH.sub.2                                         Io.191                                                                             CH.sub.2 CH(OCOCH.sub.3)CONHCH.sub.3                                       Io.192                                                                             CH.sub.2 CH(OCOCH.sub.3)CONH-cyclopropyl                                   Io.193                                                                             CH.sub.2 CH(NH.sub.2)COOH                                                  Io.194                                                                             CH.sub.2 CH(NH.sub.2)COOCH.sub.3                                           Io.195                                                                             CH.sub.2 CH(NH.sub.2)COOC.sub.2 H.sub.5                                    Io.196                                                                             CH.sub.2 CH(NH.sub.2)COOC(CH.sub.3).sub.3                                  Io.197                                                                             CH.sub.2 CH(NH.sub.2)CONH.sub.2                                            Io.198                                                                             CH.sub.2 CH(NH.sub.2)CONHCH.sub.3                                          Io.199                                                                             CH.sub.2 CH(N.sub.3)COOH                                                   Io.200                                                                             CH.sub.2 CH(N.sub.3)COOCH.sub.3                                            Io.201                                                                             CH.sub.2 CH(N.sub.3)COOC.sub.2 H.sub.5                                     Io.202                                                                             CH.sub.2 CH(N.sub.3)COOC(CH.sub.3).sub.3                                   Io.203                                                                             CH.sub.2 CH(N.sub.3)CONH.sub.2                                             Io.204                                                                             CH.sub.2 CH(N.sub.3)CONHCH.sub.3                                           Io.205                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOH                                              Io.206                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOCH.sub.3                                       Io.207                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC.sub.2 H.sub.5                                Io.208                                                                             CH.sub.2 CH(NHCOCH.sub.3)COOC(CH.sub.3).sub.3                              Io.209                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONH.sub.2                                        Io.210                                                                             CH.sub.2 CH(NHCOCH.sub.3)CONHCH.sub.3                                      Io.211                                                                             CH.sub.2 CH.sub.2 -cyclohexyl                                              Io.212                                                                             CH.sub.2 CH.sub.2 -cyclopentyl                                             Io.213                                                                             CH.sub.2 CH.sub.2 -cyclopropyl                                             Io.214                                                                             CH.sub.2 CH.sub.2 -phenyl                                                  Io.215                                                                             CHC(CN)COOC.sub.2 H.sub.5                                                  Io.216                                                                             CHC(CN)COOCH(CH.sub.3).sub.2                                               Io.217                                                                             CHC(CN)COOC(CH.sub.3).sub.3                                                Io.218                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCH.sub.2                                 Io.219                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2 CHCHCl                                     Io.220                                                                             CHC(Cl)COOCH.sub.2 CHNOCH.sub.2                                                (4-chlorophenyl)                                                           Io.221                                                                             CHC(Cl)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Io.222                                                                             CHC(Cl)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Io.223                                                                             CHC(Cl)CONH-cyclohexyl                                                     Io.224                                                                             CHC(Cl)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Io.225                                                                             CHC(Cl)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Io.226                                                                             CHC(Cl)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Io.227                                                                             CHC(Cl)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Io.228                                                                             CHC(Cl)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Io.229                                                                             CHC(Cl)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Io.230                                                                             CHC(Cl)CON(CN)-cyclopropyl                                                 Io.231                                                                             CHC(Cl)CON(CN)CH.sub.2 CHCH.sub.2                                          Io.232                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Io.233                                                                             CHC(Cl)CON(CONH.sub.2)-cyclopropyl                                         Io.234                                                                             CHC(Cl)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Io.235                                                                             CHC(Br)COOCH.sub.2 CHNOCH.sub.2                                                (4-chlorophenyl)                                                           Io.236                                                                             CHC(Br)COOCH.sub.2 CHN                                                         OCH(CH.sub.3)-(4-chlorophenyl)                                             Io.237                                                                             CHC(Br)COO-(4-acetoxytetrahydro-                                               furan-3-yl)                                                                Io.238                                                                             CHC(Br)CONH-cyclohexyl                                                     Io.239                                                                             CHC(Br)CON(CH.sub.3)CH.sub.2 COOC.sub.2 H.sub.5                            Io.240                                                                             CHC(Br)CONHCH(CH(CH.sub.3).sub.2)COOC.sub.2 H.sub.5                        Io.241                                                                             CHC(Br)CONHCH(CH.sub.2 CH(CH.sub.3).sub.2)CO                                   OCH.sub.3                                                                  Io.242                                                                             CHC(Br)CO(2-methoxycarbonyl-                                                   pyrrolidin-1-yl)                                                           Io.243                                                                             CHC(Br)CONH-(tetrahydro-                                                       furan-2-on-3-yl)                                                           Io.244                                                                             CHC(Br)CON(CN)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                            Io.245                                                                             CHC(Br)CON(CN)-cyclopropyl                                                 Io.246                                                                             CHC(Br)CON(CN)CH.sub.2 CHCH.sub.2                                          Io.247                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CH.sub.2 C.sub.2 H.sub.5                    Io.248                                                                             CHC(Br)CON(CONH.sub.2)-cyclopropyl                                         Io.249                                                                             CHC(Br)CON(CONH.sub.2)CH.sub.2 CHCH.sub.2                                  Io.250                                                                             CH.sub.2 CH(Cl)CON(C.sub.2 H.sub.5).sub.2                                  Io.251                                                                             CH.sub.2 CH(Br)CON(C.sub.2 H.sub.5).sub.2                                  Io.252                                                                             CHC(Br)CON(C.sub.2 H.sub.5).sub.2                                          Io.253                                                                             CHC(Cl)CON(C.sub.2 H.sub.5).sub.2                                          Io.254                                                                              ##STR201##                                                                Io.255                                                                              ##STR202##                                                                Io.256                                                                              ##STR203##                                                                Io.257                                                                              ##STR204##                                                                Io.258                                                                              ##STR205##                                                                Io.259                                                                              ##STR206##                                                                Io.260                                                                              ##STR207##                                                                Io.261                                                                              ##STR208##                                                                Io.262                                                                              ##STR209##                                                                __________________________________________________________________________

                  TABLE 16                                                         ______________________________________                                          ##STR210##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Ip.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Ip.002 CH.sub.2CH(CN)CONH.sub.2                                                Ip.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Ip.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Ip.005 CH.sub.2CH(C1)CONH.sub.2                                                Ip.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Ip.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Ip.008 CH.sub.2CH(Br)COOCH.sub.3                                               Ip.009 CH.sub.2CH(Br)CONH.sub.2                                                Ip.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Ip.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Ip.012 CHC(Cl)CONH.sub.2                                                       Ip.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Ip.014 CHC(Br)COOC.sub.2 H.sub.5                                               Ip.015 CHC(Br)CONH.sub.2                                                       Ip.016 CHC(Br)CON(CH.sub.3).sub.2                                              Ip.017 CHC(CN)COOC.sub.2 H.sub.5                                               Ip.018 CHC(CN)CONH.sub.2                                                       Ip.019 CHC(CN)CON(CH.sub.3).sub.2                                              Ip.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Ip.021 CHC(CH.sub.3)CONH.sub.2                                                 Ip.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 17                                                         ______________________________________                                          ##STR211##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iq.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iq.002 CH.sub.2CH(CN)CONH.sub.2                                                Iq.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iq.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iq.005 CH.sub.2CH(C1)CONH.sub.2                                                Iq.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iq.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iq.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iq.009 CH.sub.2CH(Br)CONH.sub.2                                                Iq.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iq.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iq.012 CHC(Cl)CONH.sub.2                                                       Iq.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iq.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iq.015 CHC(Br)CONH.sub.2                                                       Iq.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iq.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iq.018 CHC(CN)CONH.sub.2                                                       Iq.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iq.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iq.021 CHC(CH.sub.3)CONH.sub.2                                                 Iq.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 18                                                         ______________________________________                                          ##STR212##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Ir.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Ir.002 CH.sub.2CH(CN)CONH.sub.2                                                Ir.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Ir.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Ir.005 CH.sub.2CH(C1)CONH.sub.2                                                Ir.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Ir.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Ir.008 CH.sub.2CH(Br)COOCH.sub.3                                               Ir.009 CH.sub.2CH(Br)CONH.sub.2                                                Ir.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Ir.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Ir.012 CHC(Cl)CONH.sub.2                                                       Ir.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Ir.014 CHC(Br)COOC.sub.2 H.sub.5                                               Ir.015 CHC(Br)CONH.sub.2                                                       Ir.016 CHC(Br)CON(CH.sub.3).sub.2                                              Ir.017 CHC(CN)COOC.sub.2 H.sub.5                                               Ir.018 CHC(CN)CONH.sub.2                                                       Ir.019 CHC(CN)CON(CH.sub.3).sub.2                                              Ir.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Ir.021 CHC(CH.sub.3)CONH.sub.2                                                 Ir.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 19                                                         ______________________________________                                          ##STR213##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Is.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Is.002 CH.sub.2CH(CN)CONH.sub.2                                                Is.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Is.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Is.005 CH.sub.2CH(C1)CONH.sub.2                                                Is.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Is.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Is.008 CH.sub.2CH(Br)COOCH.sub.3                                               Is.009 CH.sub.2CH(Br)CONH.sub.2                                                Is.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Is.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Is.012 CHC(Cl)CONH.sub.2                                                       Is.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Is.014 CHC(Br)COOC.sub.2 H.sub.5                                               Is.015 CHC(Br)CONH.sub.2                                                       Is.016 CHC(Br)CON(CH.sub.3).sub.2                                              Is.017 CHC(CN)COOC.sub.2 H.sub.5                                               Is.018 CHC(CN)CONH.sub.2                                                       Is.019 CHC(CN)CON(CH.sub.3).sub.2                                              Is.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Is.021 CHC(CH.sub.3)CONH.sub.2                                                 Is.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 20                                                         ______________________________________                                          ##STR214##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         It.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        It.002 CH.sub.2CH(CN)CONH.sub.2                                                It.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       It.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        It.005 CH.sub.2CH(C1)CONH.sub.2                                                It.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       It.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        It.008 CH.sub.2CH(Br)COOCH.sub.3                                               It.009 CH.sub.2CH(Br)CONH.sub.2                                                It.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       It.011 CHC(Cl)COOC.sub.2 H.sub.5                                               It.012 CHC(Cl)CONH.sub.2                                                       It.013 CHC(Cl)CON(CH.sub.3).sub.2                                              It.014 CHC(Br)COOC.sub.2 H.sub.5                                               It.015 CHC(Br)CONH.sub.2                                                       It.016 CHC(Br)CON(CH.sub.3).sub.2                                              It.017 CHC(CN)COOC.sub.2 H.sub.5                                               It.018 CHC(CN)CONH.sub.2                                                       It.019 CHC(CN)CON(CH.sub.3).sub.2                                              It.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         It.021 CHC(CH.sub.3)CONH.sub.2                                                 It.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 21                                                         ______________________________________                                          ##STR215##                                                                                                m.p./.sup.1 H-NMR ppm!                             No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iu.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iu.002 CH.sub.2CH(CN)CONH.sub.2                                                Iu.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iu.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iu.005 CH.sub.2CH(C1)CONH.sub.2                                                Iu.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iu.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iu.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iu.009 CH.sub.2CH(Br)CONH.sub.2                                                Iu.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iu.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iu.012 CHC(Cl)CONH.sub.2                                                       Iu.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iu.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iu.015 CHC(Br)CONH.sub.2                                                       Iu.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iu.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iu.018 CHC(CN)CONH.sub.2                                                       Iu.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iu.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iu.021 CHC(CH.sub.3)CONH.sub.2                                                 Iu.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 22                                                         ______________________________________                                          ##STR216##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iv.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iv.002 CH.sub.2CH(CN)CONH.sub.2                                                Iv.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iv.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iv.005 CH.sub.2CH(C1)CONH.sub.2                                                Iv.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iv.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iv.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iv.009 CH.sub.2CH(Br)CONH.sub.2                                                Iv.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iv.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iv.012 CHC(Cl)CONH.sub.2                                                       Iv.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iv.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iv.015 CHC(Br)CONH.sub.2                                                       Iv.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iv.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iv.018 CHC(CN)CONH.sub.2                                                       Iv.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iv.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iv.021 CHC(CH.sub.3)CONH.sub.2                                                 Iv.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 23                                                         ______________________________________                                          ##STR217##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iw.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iw.002 CH.sub.2CH(CN)CONH.sub.2                                                Iw.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iw.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iw.005 CH.sub.2CH(C1)CONH.sub.2                                                Iw.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iw.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iw.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iw.009 CH.sub.2CH(Br)CONH.sub.2                                                Iw.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iw.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iw.012 CHC(Cl)CONH.sub.2                                                       Iw.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iw.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iw.015 CHC(Br)CONH.sub.2                                                       Iw.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iw.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iw.018 CHC(CN)CONH.sub.2                                                       Iw.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iw.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iw.021 CHC(CH.sub.3)CONH.sub.2                                                 Iw.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 24                                                         ______________________________________                                          ##STR218##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Ix.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Ix.002 CH.sub.2CH(CN)CONH.sub.2                                                Ix.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Ix.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Ix.005 CH.sub.2CH(C1)CONH.sub.2                                                Ix.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Ix.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Ix.008 CH.sub.2CH(Br)COOCH.sub.3                                               Ix.009 CH.sub.2CH(Br)CONH.sub.2                                                Ix.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Ix.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Ix.012 CHC(Cl)CONH.sub.2                                                       Ix.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Ix.014 CHC(Br)COOC.sub.2 H.sub.5                                               Ix.015 CHC(Br)CONH.sub.2                                                       Ix.016 CHC(Br)CON(CH.sub.3).sub.2                                              Ix.017 CHC(CN)COOC.sub.2 H.sub.5                                               Ix.018 CHC(CN)CONH.sub.2                                                       Ix.019 CHC(CN)CON(CH.sub.3).sub.2                                              Ix.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Ix.021 CHC(CH.sub.3)CONH.sub.2                                                 Ix.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 25                                                         ______________________________________                                          ##STR219##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iy.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iy.002 CH.sub.2CH(CN)CONH.sub.2                                                Iy.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iy.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iy.005 CH.sub.2CH(C1)CONH.sub.2                                                Iy.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iy.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iy.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iy.009 CH.sub.2CH(Br)CONH.sub.2                                                Iy.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iy.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iy.012 CHC(Cl)CONH.sub.2                                                       Iy.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iy.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iy.015 CHC(Br)CONH.sub.2                                                       Iy.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iy.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iy.018 CHC(CN)CONH.sub.2                                                       Iy.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iy.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iy.021 CHC(CH.sub.3)CONH.sub.2                                                 Iy.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 26                                                         ______________________________________                                          ##STR220##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iz.001 CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iz.002 CH.sub.2CH(CN)CONH.sub.2                                                Iz.003 CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iz.004 CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iz.005 CH.sub.2CH(C1)CONH.sub.2                                                Iz.006 CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iz.007 CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iz.008 CH.sub.2CH(Br)COOCH.sub.3                                               Iz.009 CH.sub.2CH(Br)CONH.sub.2                                                Iz.010 CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iz.011 CHC(Cl)COOC.sub.2 H.sub.5                                               Iz.012 CHC(Cl)CONH.sub.2                                                       Iz.013 CHC(Cl)CON(CH.sub.3).sub.2                                              Iz.014 CHC(Br)COOC.sub.2 H.sub.5                                               Iz.015 CHC(Br)CONH.sub.2                                                       Iz.016 CHC(Br)CON(CH.sub.3).sub.2                                              Iz.017 CHC(CN)COOC.sub.2 H.sub.5                                               Iz.018 CHC(CN)CONH.sub.2                                                       Iz.019 CHC(CN)CON(CH.sub.3).sub.2                                              Iz.020 CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iz.021 CHC(CH.sub.3)CONH.sub.2                                                 Iz.022 CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 27                                                         ______________________________________                                          ##STR221##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iα.001                                                                          CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iα.002                                                                          CH.sub.2CH(CN)CONH.sub.2                                                Iα.003                                                                          CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iα.004                                                                          CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iα.005                                                                          CH.sub.2CH(C1)CONH.sub.2                                                Iα.006                                                                          CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iα.007                                                                          CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iα.008                                                                          CH.sub.2CH(Br)COOCH.sub.3                                               Iα.009                                                                          CH.sub.2CH(Br)CONH.sub.2                                                Iα.010                                                                          CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iα.011                                                                          CHC(Cl)COOC.sub.2 H.sub.5                                               Iα.012                                                                          CHC(Cl)CONH.sub.2                                                       Iα.013                                                                          CHC(Cl)CON(CH.sub.3).sub.2                                              Iα.014                                                                          CHC(Br)COOC.sub.2 H.sub.5                                               Iα.015                                                                          CHC(Br)CONH.sub.2                                                       Iα.016                                                                          CHC(Br)CON(CH.sub.3).sub.2                                              Iα.017                                                                          CHC(CN)COOC.sub.2 H.sub.5                                               Iα.018                                                                          CHC(CN)CONH.sub.2                                                       Iα.019                                                                          CHC(CN)CON(CH.sub.3).sub.2                                              Iα.020                                                                          CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iα.021                                                                          CHC(CH.sub.3)CONH.sub.2                                                 Iα.022                                                                          CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 28                                                         ______________________________________                                          ##STR222##                                                                                                m.p./                                                                          .sup.1 H-NMR ppm!/                                 No.    R.sup.1              MS  mz.sup.-1 !                                    ______________________________________                                         Iβ.001                                                                           CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                        Iβ.002                                                                           CH.sub.2CH(CN)CONH.sub.2                                                Iβ.003                                                                           CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                       Iβ.004                                                                           CH.sub.2CH(C1)COOC.sub.2 H.sub.5                                        Iβ.005                                                                           CH.sub.2CH(C1)CONH.sub.2                                                Iβ.006                                                                           CH.sub.2CH(C1)CON(CH.sub.3).sub.2                                       Iβ.007                                                                           CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                        Iβ.008                                                                           CH.sub.2CH(Br)COOCH.sub.3                                               Iβ.009                                                                           CH.sub.2CH(Br)CONH.sub.2                                                Iβ.010                                                                           CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                       Iβ.011                                                                           CHC(Cl)COOC.sub.2 H.sub.5                                               Iβ.012                                                                           CHC(Cl)CONH.sub.2                                                       Iβ.013                                                                           CHC(Cl)CON(CH.sub.3).sub.2                                              Iβ.014                                                                           CHC(Br)COOC.sub.2 H.sub.5                                               Iβ.015                                                                           CHC(Br)CONH.sub.2                                                       Iβ.016                                                                           CHC(Br)CON(CH.sub.3).sub.2                                              Iβ.017                                                                           CHC(CN)COOC.sub.2 H.sub.5                                               Iβ.018                                                                           CHC(CN)CONH.sub.2                                                       Iβ.019                                                                           CHC(CN)CON(CH.sub.3).sub.2                                              Iβ.020                                                                           CHC(CH.sub.3)COOC.sub.2 H.sub.5                                         Iβ.021                                                                           CHC(CH.sub.3)CONH.sub.2                                                 Iβ.022                                                                           CHC(CH.sub.3)CON(CH.sub.3).sub.2                                        ______________________________________                                    

                  TABLE 29                                                         ______________________________________                                          ##STR223##                                                                                               m.p./.sup.1 H-NMR ppm!/                             No.   R.sup.1              MS  mz.sup.-1!                                      ______________________________________                                         Iθ.001                                                                         CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                         Iθ.002                                                                         CH.sub.2CH(CN)CONH.sub.2                                                 Iθ.003                                                                         CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                        Iθ.004                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                         Iθ.005                                                                         CH.sub.2CH(Cl)CONH.sub.2                                                 Iθ.006                                                                         CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                        Iθ.007                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                         Iθ.008                                                                         CH.sub.2CH(Br)COOCH.sub.3                                                Iθ.009                                                                         CH.sub.2CH(Br)CONH.sub.2                                                 Iθ.010                                                                         CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                        Iθ.011                                                                         CHC(Cl)COOC.sub.2 H.sub.5                                                Iθ.012                                                                         CHC(Cl)CONH.sub.2                                                        Iθ.013                                                                         CHC(Cl)CON(CH.sub.3).sub.2                                               Iθ.014                                                                         CHC(Br)COOC.sub.2 H.sub.5                                                Iθ.015                                                                         CHC(Br)CONH.sub.2                                                        Iθ.016                                                                         CHC(Br)CON(CH.sub.3).sub.2                                               Iθ.017                                                                         CHC(CN)COOC.sub.2 H.sub.5                                                Iθ.018                                                                         CHC(CN)CONH.sub.2                                                        Iθ.019                                                                         CHC(CN)CON(CH.sub.3).sub.2                                               Iθ.020                                                                         CHC(CH.sub.3)COOC.sub.2 H.sub.5                                          Iθ.021                                                                         CHC(CH.sub.3)CONH.sub.2                                                  Iθ.022                                                                         CHC(CH.sub.3)CON(CH.sub.3).sub.2                                         ______________________________________                                    

                  TABLE 30                                                         ______________________________________                                          ##STR224##                                                                                               m.p./.sup.1 H-NMR ppm!/                             No.   R.sup.1              MS  mz.sup.-1!                                      ______________________________________                                         Iπ.001                                                                            CH.sub.2CH(CN)COOC.sub.2 H.sub.5                                         Iπ.002                                                                            CH.sub.2CH(CN)CONH.sub.2                                                 Iπ.003                                                                            CH.sub.2CH(CN)CON(CH.sub.3).sub.2                                        Iπ.004                                                                            CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                         Iπ.005                                                                            CH.sub.2CH(Cl)CONH.sub.2                                                 Iπ.006                                                                            CH.sub.2CH(Cl)CON(CH.sub.3).sub.2                                        Iπ.007                                                                            CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                         Iπ.008                                                                            CH.sub.2CH(Br)COOCH.sub.3                                                Iπ.009                                                                            CH.sub.2CH(Br)CONH.sub.2                                                 Iπ.010                                                                            CH.sub.2CH(Br)CON(CH.sub.3).sub.2                                        Iπ.011                                                                            CHC(Cl)COOC.sub.2 H.sub.5                                                Iπ.012                                                                            CHC(Cl)CONH.sub.2                                                        Iπ.013                                                                            CHC(Cl)CON(CH.sub.3).sub.2                                               Iπ.014                                                                            CHC(Br)COOC.sub.2 H.sub.5                                                Iπ.015                                                                            CHC(Br)CONH.sub.2                                                        Iπ.016                                                                            CHC(Br)CON(CH.sub.3).sub.2                                               Iπ.017                                                                            CHC(CN)COOC.sub.2 H.sub.5                                                Iπ.018                                                                            CHC(CN)CONH.sub.2                                                        Iπ.019                                                                            CHC(CN)CON(CH.sub.3).sub.2                                               Iπ.020                                                                            CHC(CH.sub.3)COOC.sub.2 H.sub.5                                          Iπ.021                                                                            CHC(CH.sub.3)CONH.sub.2                                                  Iπ.022                                                                            CHC(CH.sub.3)CON(CH.sub.3).sub.2                                         ______________________________________                                    

                                      TABLE 31                                     __________________________________________________________________________      ##STR225##                                                                                                 m.p./.sup.1 H-NMR ppm!/                           No. R.sup.1        R.sup.3                                                                               R.sup.6                                                                           MS  mz.sup.-1!                                    __________________________________________________________________________     IΨ.001                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Br                                                                           H                                                    IΨ.002                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Br                                                                           Cl                                                   IΨ.003                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Br                                                                           F                                                    IΨ.004                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           H                                                    IΨ.005                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           Cl                                                   IΨ.006                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           F                                                    IΨ.007                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            H                                                    IΨ.008                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            Cl                                                   IΨ.009                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            F                                                    IΨ.010                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             H                                                    IΨ.011                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             Cl                                                   IΨ.012                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             F                                                    IΨ.013                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     H                                                    IΨ.014                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     Cl                                                   IΨ.015                                                                         CH.sub.2CH(Cl)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     F                                                    IΨ.016                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2Br                                                                            H                                                    IΨ.017                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2Br                                                                            Cl                                                   IΨ.018                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2Br                                                                            F                                                    IΨ.019                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           H                                                    IΨ.020                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           Cl                                                   IΨ.021                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 Cl                                                                           F                                                    IΨ.022                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            H                                                    IΨ.023                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            Cl                                                   IΨ.024                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2 F                                                                            F                                                    IΨ.025                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             H                                                    IΨ.026                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             Cl                                                   IΨ.027                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CHF.sub.2                                                                             F                                                    IΨ.028                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     H                                                    IΨ.029                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     Cl                                                   IΨ.030                                                                         CH.sub.2CH(Br)COOC.sub.2 H.sub.5                                                              CH.sub.2OCH.sub.3                                                                     F                                                    IΨ.031                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           H                                                    IΨ.032                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           Cl 8.10(s, 1H);                                                                   8.08(s, 1H);                                                                   7.63(s, 1H);                                                                   6.81(t, 1H);                                                                   5.85(s, 2H);                                                                   4.38(q, 2H);                                                                   1.40(t, 3H)                                       IΨ.033                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           F                                                    IΨ.034                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           H                                                    IΨ.035                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           Cl                                                   IΨ.036                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           F                                                    IΨ.037                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            H                                                    IΨ.038                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            Cl                                                   IΨ.039                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            F                                                    IΨ.040                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             H                                                    IΨ.041                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             Cl                                                   IΨ.042                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             F                                                    IΨ.043                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     H                                                    IΨ.044                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     Cl                                                   IΨ.045                                                                         CHC(Cl)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     F                                                    IΨ.046                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           H                                                    IΨ.047                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           Cl                                                   IΨ.048                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Br                                                                           F                                                    IΨ.049                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           H                                                    IΨ.050                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           Cl                                                   IΨ.051                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 Cl                                                                           F                                                    IΨ.052                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            H                                                    IΨ.053                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            Cl                                                   IΨ.054                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2 F                                                                            F                                                    IΨ.055                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             H                                                    IΨ.056                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             Cl                                                   IΨ.057                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CHF.sub.2                                                                             F                                                    IΨ.058                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     H                                                    IΨ.059                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     Cl                                                   IΨ.060                                                                         CHC(Br)COOCH.sub.2 H.sub.5                                                                    CH.sub.2OCH.sub.3                                                                     F                                                    __________________________________________________________________________

Use Examples

The herbicidal action of the substituted 3-phenylpyrazoles of the formula Iwas demonstrated by greenhouse experiments:

The cultivation containers used were plastic flowerpots containing loamy sand with about 3.0% of humus as a substrate. The seeds of the test plantswere sown separately according to species.

In the case of pre-emergence treatment, the active compound suspended or emulsified in water were applied directly after sowing by means of finely dispersing nozzles. The containers were lightly sprayed to promote germination and growth, and then covered with transparent plastic hoods until the plants had taken root. This covering brings about uniform germination of the test plants, provided this has not been adversely affected by the active compounds.

For post-emergence treatment, the test plants were raised, depending on thegrowth form, to a growth height of from 3 to 15 cm, and only then were treated with the active compounds suspended or emulsified in water. For this purpose, the test plants were either sown directly and cultivated in the same containers or they are first raised separately as seedlings and transplanted into the test containers a few days before treatment. The application rate for post-emergence treatment was 62.5 and 31.3 g of active substance per hectare.

The plants were kept according to species at 10°-25° C. or 20°-35° C. The period of the experiment extended over 2 to 4weeks. During this time, the plants were tended and their reaction to the individual treatments was evaluated.

Assessment was carried out on a scale from 0 to 100. On this scale 100 means no emergence of the plants or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments consisted of the following species:

    ______________________________________                                         Latin name          Common name                                                ______________________________________                                         Triticum aestivum   Winter wheat                                               Abutilon theophrasti                                                                               Velvet leaf                                                Galium aparine      Catchweed                                                                      bedstraw                                                   Solanum nigrum      Black nightshade                                           ______________________________________                                    

Applied post-emergence at an application rate of 62.5 and 31.3 g/ha a.s., compounds Nos. Ia.002 and Ia.003 gave very good control over unwanted plants. 

We claim:
 1. A substituted 3-phenylpyrazole of the formula I ##STR226## where R¹ is --C(R⁸)═C(R⁷,R¹²) withR⁸ being hydrogen, R⁷ being halogen, C₁ -C₄ -haloalkyl or C₂ -C₄ -alkenyl and R¹² being --COOR²⁹ or CO--N(R³⁴,R³⁵) whereas R²⁹,R³⁴ and R³⁵ are independently hydrogen or C₁ -C₈ -alkyl; R² is halogen; R³ is C₁ -C₄ -alkyl; R⁴ is C₁ -C₄ -haloalkoxy; R⁵ is halogen and R⁶ is hydrogen or halogen.
 2. A substituted 3-phenylpyrazole of the formula I ##STR227## where R¹ is --CH═C(R⁷,R¹²) withR⁷ being halogen and R¹² being --COOR²⁹ or CO--N(R³⁴,R³⁵) whereas R²⁹,R³⁴ and R³⁵ are independently hydrogen or C₁ -C₈ -alkyl; R² is chlorine; R³ is methyl; R⁴ is difluoromethoxy; R⁵ is chlorine and R⁶ is hydrogen, fluorine or chlorine.
 3. A herbicidal composition comprising liquid and/or solid carriers and, optionally, adjuvants, and a herbicidally effective quantity of at least one substituted 3-phenylpyrazole of the formula I as claimed in claim
 1. 4. A process for producing herbicidal compositions, which comprises mixing a herbicidcally effective quantity of at least one substituted 3-phenylpyrazole of the fomrula I as claimed in claim 1 with liquid and/or solid carriers and, optionally, adjuvants.
 5. A method of combating unwanted plant growth, which comprises applying a herbicidally active quantity of at least one substituted 3-phenylpyrazole of the formula I as claimed in claim 1 to plants, their habitat or seed. 